Compound characterization data — Ogawa et al., 2026

Hiroshige Ogawa, Xilun Wu, Siu Yeung Liu, Jie Zhang, Yuuya Nagata, Hugh Nakamura. “Doubly decarboxylative Asp-Asp stapling.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007554/v1

Compound
Identifier	3
¹H NMR (400 MHz, CDCl₃)	δ 7.62 (s, 1H), 7.51 (d, J = 7.4 Hz, 1H), 7.49 – 7.36 (m, 3H), 7.37 (s, 1H), 7.27 – 7.15 (m, 3H), 4.88 (t, J = 12.2 Hz, 1H), 4.82 (t, J = 12.2 Hz, 1H), 2.17 (s, 3H)
¹³C NMR (101 MHz, DMSO-d₆)	δ 176.71, 137.41, 128.96, 127.41, 123.92, 123.45, 120.40, 109.56, 82.39, 40.06, 27.98, 24.96
HRMS (ESI-TOF)	Calculated for C₁₉H₂₆BNNaO₃⁺ [M+Na]⁺: 350.1903, found: 350.1905
TLC	Rf = 0.3 (1:10 EtOAc:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	5
¹H NMR (400 MHz, CDCl₃)	δ 7.62 (s, 1H), 7.51 (d, J = 7.4 Hz, 1H), 7.49 – 7.36 (m, 3H), 7.37 (s, 1H), 7.27 – 7.15 (m, 3H), 4.88 (t, J = 12.2 Hz, 1H), 4.82 (t, J = 12.2 Hz, 1H), 2.17 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 165.09, 153.85, 135.86, 133.51, 132.49, 131.88, 130.95, 130.21, 129.84, 129.45, 127.71, 127.00, 125.47, 124.94, 123.44, 120.79, 112.72, 112.50, 69.30, 65.65, 22.89
HRMS (ESI-TOF)	Calculated for C₂₃H₁₈BrINO₂⁺ [M+H]⁺: 545.9566, found: 545.9572
TLC	Rf = 0.3 (1:10 Acetone:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	S12
¹H NMR (400 MHz, CDCl₃)	7.69 (d, J = 3.9 Hz, 1H), 7.17 – 7.15 (m, 1H), 7.14 (q, J = 2.7 Hz, 1H), 6.60 (d, J = 3.9 Hz, 1H), 1.51 (s, 9H), 1.44 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 176.65, 160.66, 158.26, 133.67, 128.76 (d, J = 9.7 Hz), 125.30, 115.96 (d, J = 22.9 Hz), 109.33 (d, J = 4.0 Hz), 106.14 (d, J = 24.1 Hz), 82.56, 40.00, 27.98, 24.92
¹⁹F NMR (377 MHz, CDCl₃)	δ −119.45
HRMS (ESI-TOF)	Calculated for C₁₉H₂₆BFNO₃⁺ [M+H]⁺: 346.1990, found: 346.1991
TLC	Rf = 0.3 (1:9 EtOAc:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	21
¹H NMR (400 MHz, CDCl₃)	7.50 – 7.42 (m, 4H), 7.32 – 7.20 (m, 4H), 7.01 (d, J = 3.3 Hz, 1H), 7.00 (d, J = 2.0 Hz, 1H), 6.90 (d, J = 8.6 Hz, 1H), 5.01 (d, J = 2.6 Hz, 2H), 2.28 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.00, 160.48, 158.08, 155.04, 136.45, 135.11, 134.21, 133.54, 128.02, 127.56, 126.39, 124.66, 117.35 (d, J = 8.8 Hz), 114.35, 113.59, 113.34, 112.74, 106.81 (d, J = 24.8 Hz), 74.25 (d, J = 4.4 Hz), 70.16, 25.50
¹⁹F NMR (377 MHz, CDCl₃)	δ −114.97
HRMS (ESI-TOF)	Calculated for C₂₄H₂₁BrFINO₂⁺ [M+H]⁺: 579.9784, found: 579.9788
TLC	Rf = 0.3 (1:10 Acetone:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	S16
¹H NMR (400 MHz, CDCl₃)	δ 7.64 (d, J = 3.9 Hz, 1H), 7.45 (dd, J = 8.5, 5.6 Hz, 1H), 7.01 (t, J = 8.8 Hz, 1H), 6.61 (d, J = 3.9 Hz, 1H), 1.52 (s, 9H), 1.48 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 177.32, 165.89, 163.53, 138.23 (d, J = 14.5 Hz), 124.77 (d, J = 4.0 Hz), 124.58, 121.80 (d, J = 10.5 Hz), 112.14 (d, J = 27.2 Hz), 109.79, 83.57, 40.66, 28.52, 25.74
¹⁹F NMR (376 MHz, CDCl₃)	δ −108.92
HRMS (ESI-TOF)	Calculated for C₁₉H₂₆BFNO₃⁺ [M+H]⁺: 346.1990, found: 346.1994
TLC	Rf = 0.4 (1:9 Acetone:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	20
¹H NMR (400 MHz, CDCl₃)	δ 8.38 (dd, J = 8.9, 4.6 Hz, 1H), 7.57 (dd, J = 8.8, 2.5 Hz, 1H), 7.53 (s, 1H), 7.32 – 7.25 (m, 3H), 7.25 – 7.19 (m, 2H), 7.22 – 7.11 (m, 2H), 6.97 (d, J = 8.8 Hz, 1H), 5.10 (d, J = 3.4 Hz, 1H), 2.11 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.64, 161.12, 158.72, 155.69, 137.09, 135.76, 134.85, 134.19, 133.09, 128.66, 128.20, 127.03, 125.31, 117.99 (d, J = 8.8 Hz), 115.00, 114.10 (d, J = 24.6 Hz), 113.39, 107.45 (d, J = 24.8 Hz), 74.91, 70.81, 26.13
¹⁹F NMR (377 MHz, CDCl₃)	δ −118.26
HRMS (ESI-TOF)	Calculated for C₂₄H₂₁BrFINO₂⁺ [M+H]⁺: 579.9784, found: 579.9783
TLC	Rf = 0.4 (1:9 Acetone:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	18
¹H NMR (400 MHz, DMSO-d₆)	δ 7.62 (s, 1H), 7.47 (d, J = 1.7 Hz, 1H), 7.44 (s, 1H), 7.33 (d, J = 1.7 Hz, 1H), 7.30 – 7.26 (m, 1H), 7.20 (ddd, J = 8.2, 2.4, 1.7 Hz, 1H), 7.00 (ddd, J = 9.3, 2.3, 1.4 Hz, 1H), 2.46 (s, 3H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 165.38, 162.99, 160.50, 133.54, 130.58, 127.99, 125.84 (d, J = 3.2 Hz), 124.06, 121.16, 116.69 (d, J = 24.5 Hz), 112.85 (d, J = 21.8 Hz), 66.89, 23.32
¹⁹F NMR (565 MHz, CDCl₃)	−121.13
HRMS (ESI-TOF)	Calculated for C₁₆H₁₀BrFINNaO⁺ [M+Na]⁺: 479.8872, found: 479.8875
TLC	Rf = 0.3 (1:10 Acetone:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	19
¹H NMR (400 MHz, CDCl₃)	δ 7.63 (s, 1H), 7.55 (dd, J = 6.6, 2.2 Hz, 1H), 7.48 – 7.42 (m, 2H), 7.32 (dd, J = 6.6, 2.1 Hz, 1H), 7.26 (ddd, J = 8.5, 5.0, 2.2 Hz, 1H), 7.16 (t, J = 8.4 Hz, 1H), 2.44 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 165.43, 158.55, 156.09, 138.82 (d, J = 4.4 Hz), 133.55, 131.61, 130.61, 128.91, 128.22, 127.29 (d, J = 7.0 Hz), 125.66, 124.06, 120.76, 115.54 (d, J = 22.3 Hz), 108.09 (d, J = 21.3 Hz), 66.89, 23.44
¹⁹F NMR (376 MHz, CDCl₃)	δ −109.88
HRMS (ESI-TOF)	Calculated for C₁₆H₁₀BrFINNaO⁺ [M+Na]⁺: 479.8872, found: 479.8871
TLC	Rf = 0.3 (1:10 Acetone:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	6
¹H NMR (400 MHz, CDCl₃)	δ 7.85 (dd, J = 3.0, 2.2 Hz, 2H), 7.82 – 7.73 (m, 2H), 7.34 (brs, 1H), 7.23 (brs, 1H), 7.14 (brs, 1H), 6.17 (brs, 1H), 5.04 – 4.97 (m, 1H), 4.88 – 4.77 (m, 1H), 4.79 – 4.67 (m, 1H), 4.57 – 4.53 (m, 1H), 4.22 – 4.10 (m, 2H), 3.72 (s, 3H), 3.80 – 3.62 (m, 2H), 3.15 – 2.67 (m, 5H), 2.59 – 2.44 (m, 3H), 2.04 (s, 3H), 2.10 – 1.97 (m, 2H), 1.72 – 1.60 (m, 3H), 1.43 (s, 9H), 1.00 – 0.81 (m, 8H), 0.01 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 171.73, 171.26, 171.11, 168.43, 161.57, 161.56, 155.23, 134.95, 128.92, 124.18, 80.67, 63.63, 52.89, 52.53, 52.02, 49.33, 48.63, 41.49, 37.86, 36.35, 31.60, 30.08, 29.80, 28.37, 24.82, 22.93, 22.16, 17.36, −1.42
HRMS (ESI-TOF)	Calculated for C₃₈H₅₇N₅NaO₁₃SSi⁺ [M+Na]⁺: 874.3341, found: 874.3336
[α]25D	+22.8 (c = 1.0, CHCl3)
TLC	Rf = 0.6 (1:2 EtOAc:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	S38
¹H NMR (400 MHz, MeOD)	δ 4.54 (t, J = 6.8 Hz, 1H), 4.46 – 4.42 (m, 1H), 4.14 – 4.06 (m, 1H), 3.72 (s, 3H), 2.56 – 2.51 (m, 2H), 2.10 (s, 1H), 1.95 (dd, J = 14.5, 7.5 Hz, 2H), 1.72 – 1.51 (m, 6H), 1.45 (s, 9H), 0.95 – 0.86 (m, 12H)
¹³C NMR (101 MHz, MeOD)	δ 173.47, 172.34, 171.47, 155.81, 78.55, 52.42, 51.40, 50.73, 50.09, 47.91, 39.99, 39.27, 31.05, 28.69, 26.78, 23.84, 21.48, 21.38, 20.09, 19.85, 13.33
HRMS (ESI-TOF)	Calculated for C₂₃H₄₄N₃O₆S⁺ [M+H]⁺: 490.2951, found: 490.2955
[α]25D	−16.0 (c = 0.1, CHCl3)

Compound
Identifier	S39
¹H NMR (400 MHz, MeOD)	δ 4.65 – 4.31 (m, 3H), 4.19 – 3.98 (m, 1H), 3.71 (s, 3H), 2.87 – 2.77 (m, 0H), 2.62 – 2.42 (m, 1H), 2.10 (s, 3H), 2.03 – 1.89 (m, 2H), 1.72 – 1.50 (m, 9H), 1.46 (s, 9H), 1.02 – 0.76 (m, 18H)
¹³C NMR (101 MHz, MeOD)	δ 173.67, 172.38, 171.54, 153.77, 78.56, 52.51, 51.48, 51.03, 50.70, 50.09, 39.97, 39.82, 39.24, 30.85, 28.85, 26.75, 23.82, 23.75, 21.48, 21.40, 20.13, 19.81, 13.33
HRMS (ESI-TOF)	Calculated for C₂₉H₅₅N₄O₇S⁺ [M+H]⁺: 603.3791, found: 603.3786
[α]25D	+39.9 (c = 0.1, CHCl3)

Compound
Identifier	7′
¹H NMR sample	A mixture of two rotamers
¹H NMR reporting	Signals of the major rotamer were reported
¹H NMR (400 MHz, MeOD)	δ 10.03 (s, 1H), 7.61 (d, J = 7.4 Hz, 1H), 7.50 (s, 1H), 7.46 (d, J = 8.7 Hz, 1H), 7.25 – 7.12 (m, 4H), 7.13 – 7.02 (m, 5H), 5.02 (s, 2H), 4.80 (t, J = 6.6 Hz, 1H), 4.47 – 4.34 (m, 3H), 4.24 – 4.12 (m, 2H), 3.70 (s, 3H), 3.26 (dd, J = 14.9, 4.9 Hz, 1H), 3.16 (dd, J = 14.9, 7.8 Hz, 1H), 2.94 – 2.75 (m, 3H), 2.28 (d, J = 8.7 Hz, 2H), 1.96 (s, 3H), 1.90 (d, J = 9.0 Hz, 1H), 1.84 – 1.74 (m, 1H), 1.70 – 1.53 (m, 3H), 1.39 (s, 9H), 1.05 – 0.82 (m, 8H), 0.03 (s, 9H)
¹³C NMR sample	A mixture of two rotamers
¹³C NMR (101 MHz, MeOD)	δ 173.45, 172.30, 171.54, 170.39, 169.93, 156.08, 154.64, 136.20, 134.01, 132.98, 130.42, 130.33, 127.27, 126.52, 125.98, 123.37, 123.22, 121.94, 120.84, 120.80, 117.98, 117.34, 114.37, 112.18, 108.82, 78.96, 69.42, 62.26, 55.31, 52.57, 51.08, 51.00, 48.23, 39.50, 35.02, 28.78, 26.79, 23.78, 21.44, 19.96, 16.14, 13.21, −3.40
HRMS (ESI-TOF)	Calculated for C₅₁H₇₂BrN₅NaO₁₀SSi⁺ [M+Na]⁺: 1076.3850, found: 1076.3852
[α]25D	+84.9 (c = 1.0, CHCl3)
TLC	Rf = 0.6 (1:1 EtOAc:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	10
¹H NMR sample	Mixture of rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (600 MHz, CDCl₃)	δ 8.39 (s, 1H), 7.69 (d, J = 7.0 Hz, 1H), 7.59 (d, J = 2.5 Hz, 1H), 7.42 (dd, J = 8.7, 2.6 Hz, 1H), 7.29 – 7.18 (m, 5H), 7.05 (dd, J = 6.8, 2.7 Hz, 2H), 7.00 (d, J = 2.4 Hz, 1H), 6.97 (d, J = 8.8 Hz, 1H), 6.74 (d, J = 7.8 Hz, 1H), 6.48 (d, J = 8.2 Hz, 1H), 5.21 (d, J = 6.6 Hz, 1H), 4.98 (s, 2H), 4.65 (q, J = 6.9 Hz, 1H), 4.46 – 4.38 (m, 2H), 4.23 (d, J = 8.2 Hz, 1H), 3.98 (dd, J = 9.3, 5.2 Hz, 1H), 3.74 – 3.69 (m, 1H), 3.67 (s, 3H), 3.28 – 3.18 (m, 1H), 3.17 – 3.00 (m, 1H), 2.87 – 2.70 (m, 1H), 2.50 – 2.39 (m, 2H), 2.28 (dd, J = 13.9, 9.7 Hz, 1H), 2.22 – 2.15 (m, 2H), 2.00 (s, 1H), 1.94 – 1.88 (m, 3H), 1.63 (ddd, J = 14.0, 5.2, 2.5 Hz, 1H), 1.57 – 1.52 (m, 1H), 1.39 – 1.34 (m, 6H), 1.27 (s, 9H), 0.93 (s, 6H), 0.86 (d, J = 5.9 Hz, 3H), 0.82 (d, J = 7.6 Hz, 3H)
¹³C NMR sample	Mixture of rotamers
¹³C NMR (151 MHz, CDCl₃)	δ 73.00, 171.65, 171.18, 154.86, 136.37, 134.57, 134.41, 131.53, 131.17, 128.56, 127.99, 127.07, 123.67, 123.47, 121.20, 119.81, 118.86, 116.48, 114.30, 86.34, 80.31, 73.89, 71.43, 69.28, 54.07, 52.41, 51.72, 51.19, 49.14, 41.51, 40.61, 39.54, 39.03, 38.21, 35.31, 29.67, 28.61, 28.39, 28.14, 28.08, 27.93, 27.09, 26.35, 24.54, 24.22, 24.05, 22.85, 22.22, 19.95
HRMS (ESI-TOF)	Calculated for C₅₄H₇₁BBrN₅NaO₁₀S⁺ [M+Na]⁺: 1094.4096, found: 1094.4097
[α]25D	−21.5 (c = 1.0, CHCl3)
TLC	Rf = 0.5 (1:1 EtOAc:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	11
¹H NMR sample	A mixture of two rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, MeOD)	δ 9.89 (s, 1H), 8.17 (d, J = 8.6 Hz, 1H), 7.84 (s, 1H), 7.78 (s, 1H), 7.59 (d, J = 7.7 Hz, 1H), 7.38 – 7.13 (m, 6H), 7.12 – 7.01 (m, 4H), 6.84 (d, J = 7.4 Hz, 1H), 6.74 (d, J = 2.4 Hz, 1H), 5.07 (qd, J = 12.5, 2.4 Hz, 2H), 4.96 (p, J = 4.4 Hz, 1H), 4.47 – 4.35 (m, 1H), 4.20 – 4.16 (m, 1H), 3.96 (t, J = 7.5 Hz, 1H), 3.81 (s, 3H), 3.22 (d, J = 4.0 Hz, 1H), 3.18 (q, J = 5.3, 4.4 Hz, 1H), 3.02 (d, J = 4.8 Hz, 1H), 3.00 – 2.94 (m, 1H), 2.46 – 2.33 (m, 2H), 2.01 (s, 3H), 1.85 – 1.71 (m, 2H), 1.71 – 1.49 (m, 3H), 1.47 (s, 9H), 1.01 (d, J = 6.5 Hz, 3H), 0.96 (d, J = 6.6 Hz, 3H)
¹³C NMR sample	A mixture of two rotamers
¹³C NMR (101 MHz, MeOD)	172.06, 171.88, 170.63, 169.82, 155.42, 154.42, 136.85, 134.81, 134.15, 131.10, 130.99, 128.64, 127.98, 127.94, 127.30, 126.54, 126.07, 122.65, 122.39, 120.43, 117.39, 115.95, 113.36, 77.15, 69.54, 55.13, 53.02, 51.97, 50.72, 50.50, 50.47, 39.79, 38.78, 35.46, 34.30, 30.15, 28.78, 27.92, 26.75, 25.49, 25.21, 23.74, 23.60, 22.32, 21.43, 21.25, 21.04, 13.19
HRMS (ESI-TOF)	Calculated for C₄₄H₅₅N₅NaO₈S⁺ [M+Na]⁺: 836.3669, found: 836.3666
[α]25D	+65.7 (c = 1.0, CHCl3)
TLC	Rf = 0.4 (1:1 EtOAc:Hexane, Ce2(SO4)3 in phosphomolybdic acid)

Compound
Identifier	12
¹H NMR (400 MHz, MeOD)	δ 9.40 (s, 2H), 9.14 (s, 2H), 8.81 (d, J = 7.4 Hz, 2H), 8.32 (dd, J = 20.7, 8.6 Hz, 2H), 7.88 (d, J = 10.1 Hz, 2H), 4.92 – 4.88 (m, 1H), 4.62 – 4.38 (m, 2H), 3.71 (s, 3H), 3.63 – 3.54 (m, 1H), 3.52 – 3.34 (m, 2H), 3.07 – 2.77 (m, 1H), 2.62 – 2.50 (m, 2H), 2.04 (s, 3H), 1.40 (t, J = 6.7 Hz, 2H)
¹³C NMR (101 MHz, MeOD)	δ 171.95, 169.98, 166.47, 148.42, 148.32, 143.52, 136.89, 136.13, 132.12, 131.50, 131.36, 129.08, 128.54, 127.17, 122.53, 121.57, 120.99, 53.82, 51.94, 51.22, 51.01, 50.63, 29.22, 28.95, 26.00, 25.67, 16.77, 15.32, 13.02
HRMS (ESI-TOF)	Calculated for C₃₀H₃₂N₁₁O₁₂S⁺ [M+H]⁺: 770.1953, found: 770.1958
[α]25D	−89.2 (c = 1.0, MeOH)

Compound
Identifier	13
¹H NMR sample	A mixture of multiple rotamers
¹H NMR (400 MHz, MeOD)	δ 8.23 – 8.06 (m, 6H), 7.86 (s, 1H), 7.74 (t, J = 6.1 Hz, 1H), 7.63 (t, J = 3.9 Hz, 1H), 7.50 (d, J = 2.3 Hz, 1H), 7.44 (s, 1H), 7.40 – 7.24 (m, 8H), 7.08 (d, J = 7.3 Hz, 1H), 7.02 (d, J = 7.5 Hz, 2H), 6.89 (d, J = 7.7 Hz, 1H), 6.79 (d, J = 8.4 Hz, 1H), 6.41 (d, J = 9.2 Hz, 1H), 4.74 – 4.49 (m, 3H), 4.43 (d, J = 7.2 Hz, 1H), 4.39 (s, 1H), 4.30 (d, J = 5.7 Hz, 1H), 4.22 (dd, J = 5.8, 2.2 Hz, 1H), 3.71 (s, 3H), 3.16 – 2.86 (m, 8H), 2.63 – 2.39 (m, 4H), 2.38 – 2.24 (m, 4H), 2.07 (s, 3H), 2.05 (s, 3H), 1.48 – 1.42 (m, 3H), 1.29 (s, 9H), 0.93 – 0.87 (m, 6H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 181.83, 171.66, 171.59, 171.18, 159.86, 149.50, 146.53, 143.61, 138.04, 137.06, 136.59, 136.45, 134.16, 130.46, 129.26, 129.24, 129.11, 128.86, 127.76, 127.54, 127.49, 127.26, 126.03, 120.41, 120.39, 120.35, 117.48, 88.47, 69.14, 54.62, 53.79, 52.66, 52.29, 50.80, 50.78, 50.57, 41.76, 34.53, 31.04, 29.54, 29.40, 29.03, 28.95, 28.93, 28.74, 28.56, 28.44, 26.72, 25.62, 21.71, 20.60, 16.67, 15.22, 13.03, 12.97, 11.16, 3.30
HRMS (ESI-TOF)	Calculated for C₆₆H₇₆N₁₆NaO₁₉S₂⁺ [M+Na]⁺: 1483.4812, found: 1483.4817
[α]25D	+105.1 (c = 0.5, MeOH)
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	22
¹H NMR (400 MHz, CDCl₃)	δ 8.74 (s, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.58 (t, J = 1.6 Hz, 1H), 7.30 (d, J = 1.6 Hz, 1H), 7.27 – 7.16 (m, 6H), 7.04 (s, 1H), 6.99 (s, 2H), 6.40 (d, J = 7.9 Hz, 1H), 6.07 (d, J = 7.2 Hz, 1H), 5.20 (d, J = 7.3 Hz, 1H), 4.81 (dt, J = 8.1, 4.9 Hz, 1H), 4.58 (q, J = 7.4 Hz, 1H), 4.42 (q, J = 7.1 Hz, 1H), 4.28 (q, J = 10.6, 10.1 Hz, 1H), 4.22 – 4.13 (m, 2H), 3.76 (s, 3H), 3.24 (d, J = 6.9 Hz, 2H), 3.11 (dd, J = 14.1, 5.8 Hz, 1H), 2.96 (dd, J = 17.1, 5.1 Hz, 1H), 2.84 (dd, J = 17.3, 5.0 Hz, 1H), 2.73 (q, J = 9.4, 8.7 Hz, 1H), 1.78 (s, 3H), 1.45 (s, 9H), 1.04 – 0.94 (m, 2H), 0.80 (d, J = 5.4 Hz, 3H), 0.79 (d, J = 5.4 Hz, 3H), 0.05 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.15, 171.56, 171.05, 170.88, 170.61, 142.71 (d, J = 8.5 Hz), 136.58, 133.65, 129.24, 128.62, 128.17, 127.07 (d, J = 30.0 Hz), 124.27, 123.64 – 123.06 (m), 122.47, 120.45, 119.31, 118.06 (d, J = 24.4 Hz), 114.25 (d, J = 21.7 Hz), 111.11, 80.58, 63.60, 55.24, 54.24, 52.88, 52.32, 48.89, 40.59, 37.52, 36.32, 29.77, 27.79, 24.52, 22.98, 21.67, 17.33, −1.46
¹⁹F NMR (376 MHz, CDCl₃)	δ −109.82
HRMS (ESI-TOF)	Calculated for C₄₇H₆₁BrFN₅NaO₉Si⁺ [M+Na]⁺: 988.3304, found: 988.3300
[α]25D	−45.8 (c = 0.1, MeOH)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	27
¹H NMR (400 MHz, CDCl₃)	δ 8.90 (s, 1H), 7.75 (d, J = 7.9 Hz, 1H), 7.55 (s, 1H), 7.29 – 7.17 (m, 5H), 7.14 (d, J = 9.8 Hz, 4H), 6.91 (s, 1H), 6.74 (d, J = 8.8 Hz, 2H), 6.23 (s, 1H), 5.57 (d, J = 8.9 Hz, 1H), 5.51 (d, J = 8.2 Hz, 1H), 4.90 (dt, J = 8.4, 4.3 Hz, 1H), 4.40 (dq, J = 11.7, 6.6 Hz, 2H), 4.34 – 4.28 (m, 1H), 3.72 (s, 3H), 3.28 (dd, J = 13.9, 2.8 Hz, 2H), 3.03 (dt, J = 13.4, 6.5 Hz, 3H), 2.95 (dd, J = 13.5, 6.7 Hz, 1H), 1.50 (s, 9H), 1.49 – 1.35 (m, 3H), 0.84 (d, J = 3.4 Hz, 3H), 0.82 (d, J = 3.4 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 171.59, 171.52, 171.38, 170.06, 164.60, 162.15, 155.30, 141.62 (d, J = 9.9 Hz), 138.94 (d, J = 8.1 Hz), 135.59, 134.41, 129.14, 128.79, 127.03, 125.93, 123.45, 121.78, 118.43, 114.79 (d, J = 21.5 Hz), 113.72 (d, J = 21.3 Hz), 110.73, 80.02, 67.09, 56.50, 55.26, 52.95, 52.74, 51.36, 41.32, 38.19, 37.55, 29.71, 28.97, 28.39, 24.31, 22.99, 21.58, 14.13
¹⁹F NMR (376 MHz, CDCl₃)	δ −112.45
HRMS (ESI-TOF)	Calculated for C₄₁H₄₈FN₅NaO₇⁺ [M+Na]⁺: 764.3435, found: 748.3440
[α]25D	−65.7 (c = 0.1, CHCl3)

Compound
Identifier	23
¹H NMR (400 MHz, CDCl₃)	δ 8.74 (s, 1H), 7.82 (dd, J = 6.6, 2.2 Hz, 1H), 7.72 (d, J = 7.8 Hz, 1H), 7.53 (ddd, J = 8.4, 4.7, 2.3 Hz, 1H), 7.31 – 7.15 (m, 6H), 7.04 (s, 1H), 6.96 (d, J = 14.2 Hz, 3H), 6.34 (s, 1H), 6.03 (d, J = 7.2 Hz, 1H), 5.19 (d, J = 7.3 Hz, 1H), 4.80 (dt, J = 8.1, 4.9 Hz, 1H), 4.55 (q, J = 7.5 Hz, 1H), 4.41 (d, J = 7.1 Hz, 1H), 4.34 – 4.22 (m, 1H), 4.22 – 4.14 (m, 2H), 3.76 (s, 3H), 3.25 (d, J = 6.9 Hz, 2H), 3.08 (dd, J = 14.1, 5.9 Hz, 1H), 2.95 (dd, J = 17.1, 5.1 Hz, 1H), 2.84 (dd, J = 17.1, 5.0 Hz, 1H), 2.72 (d, J = 9.6 Hz, 1H), 1.75 (s, 3H), 1.45 (s, 9H), 1.07 – 0.95 (m, 2H), 0.80 (d, J = 5.5 Hz, 3H), 0.79 (d, J = 5.5 Hz, 3H), 0.05 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.21, 171.56, 171.04, 170.86, 170.61, 159.42, 157.77, 155.80, 136.62 (d, J = 3.7 Hz), 136.55, 133.89, 133.19, 129.20, 128.88 (d, J = 6.9 Hz), 128.61, 128.04, 126.97, 124.22, 123.57, 122.52, 120.47, 118.77, 117.16 (d, J = 22.3 Hz), 111.06, 109.78 (d, J = 21.1 Hz), 80.58, 68.25, 63.61, 55.29, 54.24, 52.90, 52.29, 48.88, 40.54, 38.81, 37.43, 36.31, 28.37, 24.50, 22.99, 21.64, 17.33, −1.45
¹⁹F NMR (376 MHz, CDCl₃)	δ −108.95
HRMS (ESI-TOF)	Calculated for C₄₇H₆₁BrFN₅NaO₉Si⁺ [M+Na]⁺: 988.3304, found: 988.3309
[α]25D	−58.2 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	28
¹H NMR sample	A mixture of rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, CDCl₃)	δ 8.88 (s, 1H), 7.79 (dd, J = 7.7, 2.2 Hz, 1H), 7.74 (d, J = 7.8 Hz, 1H), 7.37 (ddd, J = 7.9, 4.9, 2.2 Hz, 1H), 7.32 – 7.21 (m, 4H), 7.17 (t, J = 7.6 Hz, 1H), 7.16 – 7.08 (m, 2H), 7.08 – 7.01 (m, 1H), 6.77 (d, J = 2.4 Hz, 1H), 6.68 (d, J = 8.3 Hz, 1H), 6.09 (d, J = 3.3 Hz, 1H), 5.50 (d, J = 8.1 Hz, 1H), 5.38 (d, J = 9.2 Hz, 1H), 4.91 (dt, J = 8.4, 4.3 Hz, 1H), 4.36 (dp, J = 11.6, 5.8 Hz, 2H), 4.19 – 4.12 (m, 1H), 3.76 (s, 3H), 3.30 (ddd, J = 22.4, 14.0, 4.1 Hz, 2H), 3.10 (dd, J = 14.7, 4.6 Hz, 1H), 3.04 – 2.85 (m, 3H), 1.62 – 1.48 (m, 3H), 1.49 (s, 9H), 0.82 (d, J = 6.5 Hz, 6H)
¹³C NMR sample	A mixture of rotamers
¹³C NMR (101 MHz, CDCl₃)	δ 171.15, 170.58, 170.20, 169.30, 161.10, 158.65, 154.54, 135.01, 134.73, 134.24, 132.77, 129.22, 128.74, 128.45, 128.21, 128.00 (d, J = 7.7 Hz), 126.82, 122.86, 121.41, 119.12, 117.44, 115.17 (d, J = 22.7 Hz), 110.00, 106.99 (d, J = 6.6 Hz), 79.19, 70.89, 55.87, 54.69, 52.05, 51.14, 50.44, 40.52, 38.81, 37.49, 30.12, 29.08, 27.78, 27.66, 26.39, 26.07, 25.95, 25.62, 25.49, 25.20, 23.66, 23.34, 22.29, 21.93, 21.27, 21.13
¹⁹F NMR (376 MHz, CDCl₃)	δ −120.81
HRMS (ESI-TOF)	Calculated for C₄₁H₄₈FN₅NaO₇⁺ [M+Na]⁺: 764.3435, found: 764.3434
[α]25D	−28.3 (c = 0.1, CHCl3)

Compound
Identifier	24
¹H NMR (400 MHz, CDCl₃)	δ 8.40 (s, 1H), 7.72 (dd, J = 6.8, 2.2 Hz, 1H), 7.57 (d, J = 2.5 Hz, 1H), 7.46 (dd, J = 8.8, 2.6 Hz, 1H), 7.30 – 7.14 (m, 10H), 7.08 (d, J = 3.9 Hz, 1H), 7.06 (d, J = 2.0 Hz, 1H), 7.04 (d, J = 7.6 Hz, 1H), 7.01 (d, J = 8.8 Hz, 1H), 6.96 (d, J = 2.5 Hz, 1H), 6.55 (d, J = 8.0 Hz, 1H), 6.10 (d, J = 6.8 Hz, 1H), 5.16 (d, J = 6.7 Hz, 1H), 5.00 (d, J = 3.5 Hz, 2H), 4.83 (dt, J = 8.6, 5.1 Hz, 1H), 4.64 (td, J = 8.2, 5.7 Hz, 1H), 4.42 (q, J = 6.6 Hz, 1H), 4.31 – 4.20 (m, 1H), 4.23 – 4.14 (m, 2H), 3.75 (s, 3H), 3.30 (dd, J = 14.5, 5.9 Hz, 1H), 3.24 (d, J = 7.3 Hz, 1H), 3.17 (dd, J = 13.7, 5.2 Hz, 1H), 2.95 (dd, J = 17.1, 5.1 Hz, 1H), 2.83 (dt, J = 18.3, 9.1 Hz, 2H), 1.45 (s, 9H), 1.44 – 1.22 (m, 3H), 1.04 – 0.95 (m, 2H), 0.77 (d, J = 5.6 Hz, 3H), 0.75 (d, J = 5.6 Hz, 3H), 0.05 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.37, 171.58, 170.93, 170.65, 155.95, 154.86, 136.74, 136.35, 134.62, 134.39, 131.64, 130.91, 129.48, 129.25, 128.64, 128.55, 128.45, 127.99, 127.63, 127.06, 126.86, 123.91, 123.54, 121.38, 120.05, 118.76, 116.36, 114.29, 110.43, 80.65, 71.39, 63.50, 55.35, 54.05, 52.81, 52.47, 48.88, 40.50, 37.41, 36.39, 28.38, 28.34, 24.55, 22.90, 21.79, 17.34, −1.44
HRMS (ESI-TOF)	Calculated for C₅₄H₆₈BrN₅NaO₁₀Si⁺ [M+Na]⁺: 1076.3817, found: 1076.3819
[α]25D	−13.5 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	29
¹H NMR (400 MHz, CDCl₃)	δ 8.65 (s, 1H), 7.74 (d, J = 7.9 Hz, 1H), 7.55 (s, 1H), 7.34 – 7.17 (m, 10H), 7.08 (d, J = 7.2 Hz, 2H), 6.94 (d, J = 8.4 Hz, 1H), 6.89 (dd, J = 8.5, 2.2 Hz, 1H), 6.79 (s, 1H), 6.56 (d, J = 7.6 Hz, 1H), 5.94 (s, 1H), 5.49 (d, J = 8.1 Hz, 1H), 5.37 (s, 1H), 5.09 – 4.96 (m, 2H), 4.86 (dt, J = 8.1, 4.3 Hz, 1H), 4.42 – 4.32 (m, 2H), 4.19 – 4.09 (m, 1H), 3.73 (s, 3H), 3.32 (dd, J = 13.6, 4.1 Hz, 1H), 3.20 (dd, J = 14.5, 4.3 Hz, 1H), 3.01 (td, J = 14.8, 13.9, 8.9 Hz, 2H), 2.93 – 2.80 (m, 2H), 1.49 (s, 9H), 1.28 (d, J = 12.4 Hz, 3H), 0.83 (d, J = 4.2 Hz, 3H), 0.81 (d, J = 4.2 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 171.27, 170.82, 170.56, 169.21, 156.22, 154.55, 154.35, 136.50, 135.08, 132.04, 131.94, 129.10, 128.39, 128.24, 128.02, 127.76, 127.27, 126.94, 126.81, 126.15, 122.91, 122.73, 79.21, 70.81, 69.76, 55.99, 54.59, 52.48, 51.88, 50.42, 41.62, 40.61, 37.40, 36.69, 36.04, 29.07, 27.77, 26.12, 25.99, 25.49, 25.27, 23.64, 22.84, 22.82, 22.35, 21.93, 21.29, 21.07
HRMS (ESI-TOF)	Calculated for C₄₈H₅₅N₅NaO₈⁺ [M+Na]⁺: 852.3948, found: 852.3951
[α]25D	−19.9 (c = 0.1, CHCl3)

Compound
Identifier	25
¹H NMR sample	A mixture of multiple rotamers
¹H NMR (400 MHz, MeOD)	δ 7.66 – 7.41 (m, 2H), 7.32 – 7.03 (m, 10H), 6.96 – 6.53 (m, 2H), 5.17 – 4.99 (m, 2H), 4.77 (t, J = 6.1 Hz, 1H), 4.63 (dd, J = 8.7, 5.8 Hz, 1H), 4.44 – 4.37 (m, 1H), 4.27 – 4.10 (m, 1H), 3.70 (d, J = 1.4 Hz, 1H), 3.29 – 3.12 (m, 1H), 3.02 – 2.74 (m, 5H), 1.50 – 1.36 (m, 9H), 1.44 – 1.26 (m, 3H), 1.10 – 0.80 (m, 6H), 0.04 (s, 9H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 173.57, 173.19, 172.91, 171.58, 171.01, 170.94, 170.64, 157.41, 156.47, 155.89, 155.05, 136.85, 136.81, 134.05, 131.78, 129.10, 129.05, 128.05, 127.91, 127.88, 127.85, 127.17, 126.53, 126.47, 126.36, 126.33, 124.28, 124.19, 120.18, 120.08, 118.77, 114.97, 114.85, 112.42, 111.82, 110.16, 107.57, 107.20, 106.94, 79.41, 79.19, 70.03, 69.99, 67.70, 62.89, 62.85, 55.41, 54.20, 52.14, 51.82, 51.75, 51.69, 51.64, 51.48, 40.50, 40.35, 38.77, 38.29, 37.05, 36.01, 35.64, 35.61, 34.67, 30.22, 29.35, 28.74, 27.37, 27.33, 27.27, 24.42, 24.34, 24.20, 23.55, 22.64, 22.35, 22.04, 21.98, 20.84, 20.70, 20.51, 16.78, 16.73, −2.80, −2.83, −2.87, −2.89
HRMS (ESI-TOF)	Calculated for C₅₄H₆₇BrFN₅NaO₁₀Si⁺ [M+Na]⁺: 1094.3722, found: 1094.3726
[α]25D	−87.6 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	30
¹H NMR sample	A mixture of two rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, CDCl₃)	δ 8.48 (s, 1H), 7.70 (dd, J = 8.6, 4.7 Hz, 1H), 7.53 (s, 1H), 7.36 – 7.16 (m, 10H), 7.08 (d, J = 7.0 Hz, 1H), 7.04 – 6.96 (m, 1H), 6.92 – 6.85 (m, 1H), 6.64 (s, 1H), 6.44 (d, J = 7.3 Hz, 1H), 5.83 (s, 1H), 5.56 (d, J = 8.0 Hz, 1H), 5.23 – 4.95 (m, 3H), 4.88 – 4.81 (m, 2H), 4.34 (dtd, J = 23.1, 8.7, 8.1, 4.8 Hz, 2H), 4.07 – 4.02 (m, 1H), 3.72 (s, 3H), 3.30 (dd, J = 13.4, 3.9 Hz, 1H), 3.18 (dd, J = 14.3, 4.7 Hz, 1H), 3.06 (dd, J = 14.2, 3.6 Hz, 1H), 2.98 (dd, J = 13.4, 7.5 Hz, 1H), 2.88 – 2.71 (m, 2H), 1.47 (s, 9H), 1.45 – 1.17 (m, 3H), 0.83 (d, J = 4.7 Hz, 3H), 0.81 (d, J = 4.7 Hz, 3H)
¹³C NMR sample	A mixture of two rotamers
¹³C NMR (101 MHz, MeOD)	δ 172.93, 172.90, 172.75, 171.24, 171.19, 156.66, 156.34, 155.25, 154.25, 137.19, 136.93, 136.81, 136.73, 133.34, 133.11, 131.56, 130.12, 129.74, 129.07, 128.96, 128.81, 128.28, 128.15, 128.01, 127.95, 127.65, 127.23, 127.19, 126.71, 126.59, 126.32, 115.20, 113.52, 112.84, 111.31, 111.22, 110.25, 109.25, 108.99, 103.98, 103.76, 101.10, 85.88, 79.39, 77.77, 73.08, 70.49, 70.16, 68.49, 54.13, 53.90, 52.03, 51.38, 51.22, 51.17, 51.14, 49.34, 40.45, 39.42, 38.39, 37.84, 37.80, 37.34, 34.92, 29.35, 28.71, 27.74, 27.58, 27.29, 27.06, 26.12, 25.80, 24.29, 23.18, 22.94, 22.03, 20.68
¹⁹F NMR (377 MHz, CDCl₃)	δ −122.54
HRMS (ESI-TOF)	Calculated for C₄₈H₅₄FN₅NaO₈⁺ [M+Na]⁺: 870.3854, found: 870.3855
[α]25D	−31.7 (c = 0.1, CHCl3)

Compound
Identifier	26
¹H NMR sample	A mixture of multiple rotamers
¹H NMR (400 MHz, MeOD)	δ 7.43 – 6.95 (m, 16H), 5.27 (s, 1H), 5.08 (s, 1H), 4.80 – 4.74 (m, 1H), 4.65 – 4.58 (m, 1H), 4.43 – 4.28 (m, 2H), 4.25 – 4.12 (m, 2H), 3.70 (s, 3H), 3.25 – 3.03 (m, 3H), 2.97 – 2.75 (m, 3H), 1.45 (s, 9H), 1.42 – 1.33 (m, 3H), 1.08 – 0.79 (m, 8H), 0.03 (s, 9H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 173.01, 172.90, 171.53, 170.94, 170.67, 158.97, 156.29, 156.15, 155.26, 154.25, 137.19, 136.91, 136.79, 136.74, 133.32, 133.11, 131.56, 128.98, 128.28, 128.05, 127.94, 127.65, 127.20, 126.59, 126.35, 115.15, 113.51, 111.21, 109.26, 103.96, 102.59, 101.13, 87.45, 87.09, 79.40, 70.47, 70.14, 62.98, 62.89, 54.24, 51.75, 51.69, 51.67, 40.44, 37.04, 35.64, 31.67, 29.35, 29.07, 27.34, 27.26, 24.27, 22.02, 20.67, 16.72, −2.89
HRMS (ESI-TOF)	Calculated for C₅₄H₆₇BrFN₅NaO₁₀Si⁺ [M+Na]⁺: 1094.3722, found: 1094.3720
[α]25D	−35.8 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	31
¹H NMR sample	A mixture of multiple rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, MeOD, 60 °C)	δ 9.90 (s, 1H), 7.84 (s, 1H), 7.71 (s, 1H), 7.34 – 7.16 (m, 10H), 7.09 (d, J = 8.4 Hz, 1H), 6.99 (d, J = 8.4 Hz, 1H), 6.91 (s, 1H), 6.84 (s, 1H), 5.16 – 5.02 (m, 2H), 4.70 – 4.54 (m, 2H), 4.44 – 4.38 (m, 1H), 4.18 (dt, J = 17.9, 6.1 Hz, 1H), 3.69 (s, 3H), 3.20 – 2.90 (m, 6H), 2.36 (q, J = 9.3, 8.7 Hz, 1H), 2.10 – 1.96 (m, 2H), 1.45 (s, 9H), 0.96 – 0.83 (m, 6H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, DMSO-d₆)	δ 175.47, 173.40, 170.27, 167.20, 155.12, 155.00, 154.84, 136.96, 134.42, 128.93, 128.76, 128.45, 128.21, 128.06, 127.81, 127.57, 127.03, 126.39, 126.21, 122.80, 106.73, 85.11, 78.84, 78.10, 76.71, 69.54, 69.39, 64.59, 57.33, 56.76, 51.81, 51.64, 50.53, 50.04, 48.64, 42.16, 42.03, 37.54, 37.38, 34.72, 34.36, 28.08, 28.05, 27.95, 27.90, 27.84, 26.62, 25.56, 25.31, 25.27, 23.42, 22.83, 21.87, 18.96, 17.18, 13.28
¹⁹F NMR (376 MHz, CDCl₃)	δ −124.77
HRMS (ESI-TOF)	Calculated for C₄₈H₅₄FN₅NaO₈⁺ [M+Na]⁺: 870.3854, found: 870.3850
[α]25D	−56.8 (c = 0.02, CHCl3)

Compound
Identifier	37
¹H NMR sample	A mixture of two rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, MeOD)	δ 8.02 (s, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.58 (s, 1H), 7.53 (d, J = 8.3 Hz, 1H), 7.37 (s, 1H), 7.35 – 7.22 (m, 5H), 7.15 (d, J = 8.6 Hz, 1H), 6.91 (d, J = 8.9 Hz, 1H), 5.95 (s, 1H), 5.18 (s, 2H), 4.82 – 4.76 (m, 1H), 4.43 – 4.37 (m, 1H), 4.28 (q, J = 5.1 Hz, 1H), 4.22 (t, J = 8.4 Hz, 1H), 4.18 – 4.09 (m, 2H), 3.74 (s, 3H), 3.25 (dd, J = 14.7, 5.4 Hz, 1H), 3.06 (dd, J = 14.8, 8.7 Hz, 1H), 2.89 – 2.77 (m, 2H), 1.69 – 1.52 (m, 3H), 1.30 (s, 9H), 1.25 (d, J = 7.4 Hz, 3H), 1.06 – 0.98 (m, 2H), 0.92 (d, J = 5.8 Hz, 3H), 0.89 (d, J = 5.4 Hz, 3H), 0.07 (s, 9H)
¹³C NMR sample	A mixture of two rotamers
¹³C NMR (101 MHz, MeOD)	δ 173.05, 171.72, 171.29, 170.98, 170.65, 170.51, 156.49, 156.27 (d, J = 4.5 Hz), 155.52, 136.61, 134.01, 133.47, 133.05, 132.38, 128.23 (d, J = 9.9 Hz), 128.11, 127.47, 126.85, 124.67, 115.74, 112.90, 111.46, 109.61 (d, J = 25.7 Hz), 108.55 (d, J = 3.3 Hz), 103.20 (d, J = 23.9 Hz), 79.71, 70.64, 62.82, 51.63, 48.94, 40.04, 35.81, 35.60, 29.36, 27.23, 24.40, 22.08, 20.94, 20.91, 20.33, 16.74, 16.71, 16.21, −2.88
¹⁹F NMR (377 MHz, MeOD)	δ −126.77
HRMS (ESI-TOF)	Calculated for C₄₈H₆₃BrFN₅NaO₁₀Si⁺ [M+Na]⁺: 1018.3409, found: 1018.3414
[α]25D	+4.7 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	41
¹H NMR sample	A mixture of multiple rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, MeOD, 60 °C)	δ 7.69 (s, 1H), 7.40 (s, 1H), 7.37 – 7.15 (m, 8H), 7.14 (d, J = 8.6 Hz, 1H), 6.91 (d, J = 8.7 Hz, 1H), 5.15 (d, J = 16.1 Hz, 1H), 5.02 (d, J = 11.9 Hz, 1H), 4.63 – 4.24 (m, 3H), 4.17 (q, J = 7.3 Hz, 1H), 3.78 (s, 3H), 3.76 – 3.61 (m, 2H), 3.08 (t, J = 13.3 Hz, 1H), 3.06 – 2.95 (m, 1H), 2.06 (dd, J = 16.9, 9.6 Hz, 1H), 1.73 – 1.55 (m, 2H), 1.31 (s, 9H), 0.92 (d, J = 15.3 Hz, 3H), 0.86 (d, J = 7.6 Hz, 3H), 0.84 (d, J = 6.5 Hz, 3H)
¹³C NMR (101 MHz, MeOD)	δ 174.38, 173.35, 173.31, 171.42, 158.16, 156.52, 155.86, 154.35, 136.50, 133.33, 132.73, 132.39, 131.69, 131.57, 128.85, 127.45, 127.39, 126.70, 126.33, 120.98, 114.40, 110.70, 110.60, 108.87, 108.60, 107.40, 102.12, 101.88, 78.89, 70.60, 66.10, 60.79, 53.87, 52.64, 50.86, 50.80, 50.75, 38.65, 34.32, 31.03, 29.77, 28.71, 26.51, 26.32, 23.86, 21.56, 19.21, 14.97
¹⁹F NMR (377 MHz, MeOD)	δ −127.50
HRMS (ESI-TOF)	Calculated for C₄₂H₅₀FN₅NaO₈⁺ [M+Na]⁺: 794.3541, found: 794.3536
[α]25D	+36.3 (c = 0.1, CHCl3)
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	38
¹H NMR sample	A mixture of multiple rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (600 MHz, MeOD)	δ 7.43 – 6.94 (m, 10H), 6.92 – 6.76 (m, 1H), 5.26 – 4.98 (m, 2H), 4.74 (dt, J = 8.8, 6.1 Hz, 1H), 4.45 – 4.36 (m, 2H), 4.25 – 4.03 (m, 3H), 3.68 (s, 3H), 3.21 – 2.98 (m, 1H), 2.85 – 2.75 (m, 3H), 1.83 – 1.78 (m, 1H), 1.67 – 1.50 (m, 5H), 1.42 (s, 9H), 0.95 – 0.85 (m, 14H), 0.03 (s, 9H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 171.83, 171.63, 171.38, 170.76, 170.38, 169.87, 169.76, 155.69, 155.11, 137.00, 136.97, 136.76, 132.81, 132.27, 128.31, 128.25, 128.16, 128.11, 128.01, 127.95, 127.60, 127.41, 127.10, 126.94, 114.16, 113.06, 78.12, 78.00, 74.25, 69.40, 62.27, 56.29, 51.98, 50.36, 48.28, 48.18, 40.54, 36.72, 36.54, 35.76, 35.50, 28.77, 27.93, 27.87, 27.82, 27.78, 27.62, 23.99, 23.90, 23.86, 23.82, 22.69, 22.67, 22.58, 21.37, 21.30, 16.55, 14.96, 14.88, 10.81, 10.76, 10.70, −1.73
¹⁹F NMR (565 MHz, MeOD)	δ −127.46
HRMS (ESI-TOF)	Calculated for C₅₁H₆₉BrFN₅NaO₁₀Si⁺ [M+Na]⁺: 1060.3879, found: 1060.3882
[α]25D	+18.9 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	42
¹H NMR (400 MHz, CDCl₃)	δ 9.59 (s, 1H), 7.89 (d, J = 2.1 Hz, 1H), 7.38 (d, J = 5.7 Hz, 3H), 7.30 (d, J = 8.2 Hz, 2H), 7.28 – 7.17 (m, 3H), 7.10 (t, J = 5.7 Hz, 2H), 6.94 (td, J = 9.0, 2.5 Hz, 1H), 6.85 (d, J = 8.5 Hz, 1H), 6.59 (d, J = 5.8 Hz, 1H), 5.15 (d, J = 11.1 Hz, 1H), 5.05 (d, J = 11.1 Hz, 1H), 4.89 – 4.80 (m, 2H), 4.52 (ddt, J = 13.2, 7.7, 4.0 Hz, 1H), 4.37 (dt, J = 10.8, 3.7 Hz, 1H), 4.33 (dd, J = 5.8, 3.7 Hz, 1H), 3.93 (dd, J = 15.9, 3.0 Hz, 1H), 3.77 (s, 3H), 3.34 (dd, J = 14.7, 3.2 Hz, 1H), 3.21 – 3.02 (m, 2H), 2.10 – 1.99 (m, 1H), 1.75 (ddd, J = 14.1, 10.8, 3.2 Hz, 1H), 1.48 – 1.35 (m, 4H), 1.29 (s, 9H), 0.98 (d, J = 6.9 Hz, 3H), 0.91 (t, J = 7.1 Hz, 3H), 0.82 (d, J = 6.4 Hz, 3H), 0.80 (d, J = 6.4 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 173.20, 173.15, 171.66, 169.54, 135.56, 132.49, 131.65, 130.66, 130.33, 128.27, 128.05 (d, J = 7.9 Hz), 127.95, 126.98, 114.15, 111.13 (d, J = 9.5 Hz), 110.17 (d, J = 26.2 Hz), 107.16 (d, J = 5.3 Hz), 101.68 (d, J = 23.4 Hz), 80.99, 71.24, 59.61, 54.37, 53.65, 51.95, 50.83, 38.58, 34.91, 27.30, 26.81, 24.33, 24.07, 22.77, 19.54, 15.54, 11.24
¹⁹F NMR (377 MHz, MeOD)	δ −123.75
HRMS (ESI-TOF)	Calculated for C₄₅H₅₆FN₅NaO₈⁺ [M+Na]⁺: 836.4011, found: 836.4013
[α]25D	+26.6 (c = 0.1, CHCl3)

Compound
Identifier	39
¹H NMR sample	A mixture of multipe rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, MeOD)	δ 7.55 (d, J = 11.9 Hz, 1H), 7.50 (d, J = 8.1 Hz, 1H), 7.43 – 7.37 (m, 1H), 7.36 – 7.14 (m, 11H), 7.04 (d, J = 6.9 Hz, 1H), 7.01 – 6.88 (m, 1H), 5.15 (dd, J = 10.1, 3.8 Hz, 1H), 4.82 – 4.76 (m, 1H), 4.70 – 4.57 (m, 1H), 4.50 – 4.33 (m, 2H), 4.26 – 4.13 (m, 2H), 3.72 (s, 3H), 3.02 – 2.71 (m, 5H), 1.63 – 1.50 (m, 3H), 1.46 (s, 9H), 1.10 – 0.85 (m, 8H), 0.07 (s, 9H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 172.82, 171.53, 171.03, 171.00, 170.62, 170.56, 158.81, 156.51, 155.96, 155.44, 136.84, 136.57, 134.03, 133.06, 132.45, 130.58, 129.09, 129.04, 128.34, 128.22, 128.20, 128.12, 128.10, 127.66, 127.47, 127.13, 126.82, 126.55, 124.66, 115.91, 113.63, 112.97, 112.45, 111.53, 108.65, 103.32, 103.09, 79.78, 79.61, 70.67, 70.13, 62.88, 55.67, 54.30, 51.66, 51.61, 35.64, 29.34, 27.32, 27.20, 24.25, 24.15, 22.03, 20.64, 16.79, 16.76, −2.87
¹⁹F NMR (377 MHz, MeOD)	δ −126.58
HRMS (ESI-TOF)	Calculated for C₅₄H₆₇BrFN₅NaO₁₀Si⁺ [M+Na]⁺: 1094.3722, found: 1094.3721
[α]25D	+21.0 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	43
¹H NMR (400 MHz, CDCl₃)	δ 9.53 (d, J = 6.9 Hz, 1H), 7.80 (s, 1H), 7.36 (s, 3H), 7.35 – 7.29 (m, 2H), 7.27 (t, J = 5.6 Hz, 4H), 7.21 (dd, J = 9.7, 2.1 Hz, 1H), 7.12 (d, J = 7.5 Hz, 2H), 7.08 (d, J = 4.0 Hz, 1H), 7.08 – 7.02 (m, 1H), 6.92 (t, J = 9.1 Hz, 1H), 6.68 – 6.56 (m, 2H), 5.10 (d, J = 11.4 Hz, 1H), 4.99 (d, J = 11.3 Hz, 1H), 4.88 – 4.75 (m, 2H), 4.70 (q, J = 5.9 Hz, 1H), 4.57 (ddd, J = 12.0, 8.6, 3.1 Hz, 1H), 4.35 (dt, J = 10.8, 3.9 Hz, 1H), 3.83 (dd, J = 16.1, 3.5 Hz, 1H), 3.76 (s, 3H), 3.32 (d, J = 14.9 Hz, 1H), 3.19 (dd, J = 14.4, 6.6 Hz, 1H), 3.14 – 3.07 (m, 2H), 3.07 – 2.98 (m, 1H), 1.71 (ddd, J = 14.7, 11.0, 3.3 Hz, 1H), 1.31 – 1.18 (m, 2H), 1.16 (s, 9H), 0.85 (d, J = 6.4 Hz, 3H), 0.76 (d, J = 6.4 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 173.21, 172.92, 171.63, 169.83, 158.52, 156.10 (d, J = 16.5 Hz), 153.58, 135.56, 132.43, 130.71, 130.09, 128.52, 128.33, 128.23, 127.91 (d, J = 3.0 Hz), 127.02, 126.90, 119.08, 114.18, 111.09 (d, J = 9.4 Hz), 110.32, 110.06, 107.15 (d, J = 4.7 Hz), 101.83 (d, J = 23.9 Hz), 80.68, 71.20, 55.04, 54.24, 53.42, 51.96, 50.81, 38.54, 35.56, 34.97, 27.29, 26.84, 23.63, 22.69, 19.89
¹⁹F NMR (377 MHz, MeOD)	δ −123.72
HRMS (ESI-TOF)	Calculated for C₄₈H₅₄FN₅NaO₈⁺ [M+Na]⁺: 870.3854, found: 870.3849
[α]25D	+11.1 (c = 0.03, CHCl3)

Compound
Identifier	40
¹H NMR sample	A mixture of multipe rotamers
¹H NMR reporting	Signals of the major isomer were reported
¹H NMR (400 MHz, MeOD)	δ 8.17 – 8.05 (m, 1H), 8.02 (d, J = 7.9 Hz, 1H), 7.57 (s, 1H), 7.51 (t, J = 7.8 Hz, 1H), 7.39 – 7.23 (m, 5H), 7.14 (d, J = 8.8 Hz, 1H), 6.93 (qd, J = 9.3, 2.7 Hz, 1H), 5.20 – 5.12 (m, 2H), 4.82 – 4.75 (m, 1H), 4.52 – 4.38 (m, 2H), 4.33 (t, J = 5.9 Hz, 1H), 4.25 – 4.07 (m, 2H), 3.71 (s, 3H), 3.30 – 3.18 (m, 1H), 3.05 (dd, J = 14.7, 8.9 Hz, 1H), 2.89 – 2.82 (m, 2H), 2.42 – 2.35 (m, 2H), 2.03 (s, 3H), 2.01 – 1.85 (m, 2H), 1.72 – 1.53 (m, 3H), 1.29 (s, 9H), 1.06 – 0.85 (m, 8H), 0.03 (s, 9H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 173.85, 173.03, 172.93, 171.97, 171.02, 171.00, 170.61, 170.57, 158.79, 156.48, 156.17, 155.98, 155.49, 136.82, 136.58, 134.02, 133.57, 133.49, 133.05, 132.41, 132.20, 131.02, 130.61, 128.49, 128.34, 128.26, 128.14, 128.06, 127.67, 127.49, 127.13, 126.85, 124.65, 115.78, 113.70, 112.94, 112.51, 111.59, 111.50, 109.80, 109.54, 108.66, 103.37, 103.14, 79.68, 79.58, 70.68, 70.18, 67.72, 62.87, 55.54, 53.18, 51.68, 51.65, 40.12, 38.77, 35.63, 31.11, 30.71, 30.23, 29.56, 29.49, 29.36, 28.74, 27.35, 27.25, 24.42, 24.39, 22.05, 20.64, 20.53, 16.79, 16.76, 13.92, −2.81
¹⁹F NMR (377 MHz, MeOD)	δ −126.56
HRMS (ESI-TOF)	Calculated for C₅₀H₆₇BrFN₅NaO₁₀SSi⁺ [M+Na]⁺: 1078.3443, found: 1078.3439
[α]25D	+12.9 (c = 0.05, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	44
¹H NMR sample	A mixture of multiple rotamers
¹H NMR (400 MHz, MeOD)	δ 7.64 (s, 1H), 7.45 – 7.32 (m, 1H), 7.33 – 7.18 (m, 7H), 7.15 – 7.05 (m, 1H), 6.89 (tt, J = 9.0, 2.3 Hz, 1H), 5.18 (d, J = 9.7 Hz, 1H), 5.17 – 5.09 (m, 1H), 5.05 – 4.96 (m, 1H), 4.36 (td, J = 9.7, 8.7, 4.1 Hz, 3H), 3.76 (s, 3H), 3.66 (dd, J = 5.6, 4.2 Hz, 1H), 3.63 – 3.59 (m, 1H), 3.56 (dd, J = 5.6, 4.1 Hz, 1H), 3.49 (t, J = 6.6 Hz, 1H), 3.10 – 2.94 (m, 2H), 2.67 – 2.47 (m, 2H), 2.09 (s, 3H), 1.72 – 1.52 (m, 3H), 1.21 (s, 9H), 0.86 – 0.81 (m, 6H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 174.57, 173.01, 171.93, 171.33, 158.15, 156.45, 155.84, 154.34, 136.48, 131.57 (d, J = 10.8 Hz), 131.50, 131.04, 128.80, 127.57, 127.40, 126.71, 126.33, 120.95, 114.24, 110.68 (d, J = 9.4 Hz), 108.75 (d, J = 26.8 Hz), 102.07 (d, J = 23.8 Hz), 78.92, 71.64, 70.48, 70.09, 69.36, 69.17, 60.19, 54.27, 54.03, 52.61, 50.90, 38.63, 34.39, 30.77, 29.10, 28.73, 26.42, 23.85, 21.60, 19.22, 18.26, 15.31, 13.11, 12.20
¹⁹F NMR (377 MHz, MeOD)	δ −127.38
HRMS (ESI-TOF)	Calculated for C₄₄H₅₄FN₅NaO₈S⁺ [M+Na]⁺: 854.3575, found: 854.3576
[α]25D	+63.0 (c = 0.1, CHCl3)
NMR note	Due to the slow H-D exchange, exchange proton of the secondary amides were partially visible even when MeOD was used

Compound
Identifier	S40
¹H NMR (600 MHz, CDCl₃)	δ 8.18 (s, 1H), 7.59 (q, J = 2.5, 1.9 Hz, 2H), 7.44 (dd, J = 8.7, 2.5 Hz, 1H), 7.30 – 7.20 (m, 5H), 7.25 – 7.18 (m, 1H), 7.02 (s, 1H), 7.00 (d, J = 8.7 Hz, 1H), 6.93 (s, 1H), 5.10 (d, J = 8.3 Hz, 1H), 4.97 (s, 2H), 4.66 (dt, J = 8.3, 5.5 Hz, 1H), 3.65 (s, 3H), 3.32 (d, J = 5.5 Hz, 2H), 1.44 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.84, 155.35, 154.78, 136.25, 134.56, 131.62, 131.23, 128.60, 128.06, 127.09, 123.66, 122.98, 121.25, 119.83, 118.81, 116.60, 114.51, 110.37, 79.96, 71.61, 54.26, 52.34, 28.45, 28.15
HRMS (ESI-TOF)	Calculated for C₃₀H₃₁BrN₂NaO₅⁺ [M+Na]⁺: 601.1314, found: 601.1311
[α]25D	+23.6 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	50
¹H NMR (400 MHz, CDCl₃)	δ 8.21 (s, 1H), 7.69 (dd, J = 6.9, 2.1 Hz, 1H), 7.58 (d, J = 2.5 Hz, 1H), 7.44 (dd, J = 8.8, 2.5 Hz, 1H), 7.29 – 7.12 (m, 5H), 7.07 (d, J = 3.6 Hz, 1H), 7.06 (d, J = 2.1 Hz, 1H), 7.03 (d, J = 2.4 Hz, 1H), 6.99 (d, J = 8.8 Hz, 1H), 6.73 (d, J = 7.0 Hz, 1H), 5.14 (brs, 1H), 4.99 (s, 2H), 4.50 (dt, J = 6.9, 3.4 Hz, 1H), 4.43 (q, J = 6.5 Hz, 1H), 3.91 – 3.78 (m, 1H), 3.75 (dd, J = 11.3, 3.5 Hz, 1H), 3.69 (s, 3H), 3.41 (dd, J = 14.6, 6.1 Hz, 1H), 3.20 (dd, J = 14.6, 6.4 Hz, 1H), 1.43 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 172.05, 170.36, 155.62, 154.70, 136.19, 134.59, 134.39, 131.60, 130.89, 128.53, 128.05, 127.69, 127.13, 123.79, 123.31, 121.28, 119.89, 118.72, 116.38, 114.33, 110.45, 80.56, 71.45, 67.10, 62.72, 55.04, 52.67, 29.71, 28.30
HRMS (ESI-TOF)	Calculated for C₃₃H₃₅N₃NaO₆⁺ [M+Na]⁺: 592.2424, found: 592.2426
[α]25D	+76.1 (c = 0.01, CHCl3)

Compound
Identifier	S41
¹H NMR (400 MHz, MeOD)	δ 10.01 (s, 1H), 7.65 (d, J = 7.7 Hz, 1H), 7.47 (s, 1H), 7.45 (d, J = 7.7 Hz, 1H), 7.20 – 7.14 (m, 3H), 7.13 – 7.03 (m, 6H), 5.01 (t, J = 3.2 Hz, 2H), 4.52 – 4.43 (m, 2H), 4.14 – 4.10 (m, 1H), 3.69 (s, 3H), 3.11 (dd, J = 14.8, 7.8 Hz, 1H), 1.76 – 1.67 (m, 1H), 1.63 (dt, J = 9.3, 4.7 Hz, 1H), 1.58 – 1.50 (m, 1H), 1.44 (s, 9H), 0.95 (d, J = 6.6 Hz, 3H), 0.91 (d, J = 6.1 Hz, 3H)
¹³C NMR (101 MHz, MeOD)	δ 172.71, 172.48, 172.35, 155.76, 154.65, 136.18, 132.89, 130.39, 127.28, 126.52, 125.96, 123.19, 121.79, 120.72, 117.86, 117.31, 114.43, 112.17, 109.04, 78.64, 69.41, 54.73, 53.17, 50.76, 50.69, 50.07, 39.54, 39.36, 27.71, 27.09, 26.72, 23.91, 23.80, 23.72, 21.38, 21.31, 19.96, 19.81
HRMS (ESI-TOF)	Calculated for C₃₆H₄₂BrN₃O₆⁺ [M+Na]⁺: 691.2257, found: 691.2260
[α]25D	+31.0 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	51
¹H NMR (400 MHz, CDCl₃)	δ 8.29 (s, 1H), 7.69 (d, J = 7.2 Hz, 1H), 7.58 (d, J = 2.5 Hz, 1H), 7.44 (dd, J = 8.7, 2.5 Hz, 1H), 7.24 (q, J = 6.0, 4.4 Hz, 5H), 7.19 – 7.11 (m, 1H), 7.05 (dd, J = 6.6, 2.9 Hz, 1H), 7.03 (d, J = 2.3 Hz, 1H), 7.00 (d, J = 8.8 Hz, 1H), 6.29 (d, J = 7.9 Hz, 1H), 5.13 (s, 1H), 4.99 (s, 2H), 4.54 (dt, J = 7.8, 3.1 Hz, 1H), 4.42 (d, J = 7.4 Hz, 2H), 3.97 – 3.81 (m, 2H), 3.76 (s, 3H), 3.27 (d, J = 6.5 Hz, 2H), 1.75 (s, 1H), 1.65 – 1.53 (m, 1H), 1.41 (s, 9H), 1.27 (d, J = 10.5 Hz, 1H), 0.84 (d, J = 4.2 Hz, 3H), 0.82 (d, J = 4.0 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 171.73, 171.70, 170.91, 169.96, 155.22, 154.05, 135.56, 133.93, 133.71, 130.96, 130.23, 127.87, 127.36, 126.96, 126.37, 123.17, 122.75, 120.62, 119.40, 118.10, 115.75, 113.68, 109.56, 80.33, 70.76, 66.47, 61.85, 54.84, 54.37, 52.05, 51.13, 39.17, 27.63, 23.91, 22.13, 21.42
HRMS (ESI-TOF)	Calculated for C₃₉H₄₆N₄NaO₇⁺ [M+Na]⁺: 691.2257, found: 691.2260
[α]25D	+91.4 (c = 0.01, CHCl3)

Compound
Identifier	S42
¹H NMR (400 MHz, MeOD)	δ 9.96 (s, 1H), 8.24 (d, J = 8.1 Hz, 1H), 8.06 (s, 1H), 7.63 (d, J = 7.7 Hz, 1H), 7.47 (s, 1H), 7.45 (d, J = 10.3 Hz, 1H), 7.09 (td, J = 23.4, 22.6, 7.2 Hz, 9H), 6.59 (d, J = 7.4 Hz, 1H), 5.03 – 4.97 (m, 2H), 4.56 – 4.42 (m, 4H), 3.68 (s, 3H), 3.35 – 3.25 (m, 1H), 3.12 (dd, J = 14.7, 8.1 Hz, 1H), 2.48 (t, J = 7.8 Hz, 2H), 2.14 – 2.03 (m, 1H), 2.02 (s, 3H), 1.95 – 1.85 (m, 1H), 1.72 – 1.47 (m, 6H), 1.36 (s, 9H), 0.93 (d, J = 6.4 Hz, 4H), 0.89 (d, J = 6.2 Hz, 5H), 0.85 (d, J = 6.2 Hz, 3H)
¹³C NMR (101 MHz, MeOD)	δ 172.94, 172.48, 172.36, 171.63, 155.95, 154.63, 136.16, 132.92, 130.40, 127.26, 126.51, 125.95, 123.13, 121.86, 120.76, 117.97, 117.38, 114.44, 112.21, 109.10, 78.79, 69.44, 55.06, 51.57, 51.26, 50.72, 50.21, 50.11, 39.98, 39.23, 30.61, 28.94, 27.05, 26.73, 23.80, 23.66, 21.42, 20.35, 19.77, 13.34
HRMS (ESI-TOF)	Calculated for C₄₇H₆₂BrN₅NaO₈S⁺ [M+Na]⁺: 958.3400, found: 958.3401
[α]25D	+9.7 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	52
¹H NMR (400 MHz, CDCl₃)	δ 9.73 (s, 2H), 7.69 (d, J = 7.9 Hz, 1H), 7.39 (s, 2H), 7.26 (s, 5H), 7.18 (q, J = 7.4, 5.6 Hz, 2H), 7.08 (s, 1H), 7.06 (d, J = 8.5 Hz, 1H), 6.78 (d, J = 8.2 Hz, 1H), 6.57 (d, J = 7.8 Hz, 1H), 5.85 (d, J = 7.6 Hz, 1H), 5.74 (d, J = 9.0 Hz, 1H), 5.34 (d, J = 8.7 Hz, 1H), 5.08 (d, J = 12.1 Hz, 1H), 4.98 (d, J = 12.2 Hz, 1H), 5.06 – 4.90 (m, 1H), 4.47 (td, J = 9.1, 2.5 Hz, 1H), 4.35 – 4.27 (m, 2H), 3.94 (s, 1H), 3.79 (s, 3H), 3.26 (d, J = 18.4 Hz, 2H), 3.11 (q, J = 7.3 Hz, 3H), 2.95 (dd, J = 14.5, 9.4 Hz, 1H), 2.24 – 2.13 (m, 1H), 2.11 – 1.97 (m, 1H), 1.85 (s, 3H), 1.47 (s, 9H), 1.41 (t, J = 7.3 Hz, 6H), 0.89 (d, J = 6.5 Hz, 3H), 0.85 (d, J = 6.6 Hz, 3H), 0.83 (d, J = 4.6 Hz, 3H), 0.81 (d, J = 3.9 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 172.01, 171.23, 171.01, 170.91, 170.59, 154.71, 154.25, 154.20, 136.05, 133.94, 131.27, 131.13, 128.30, 127.82, 127.15, 126.89, 126.38, 126.19, 123.56, 123.12, 118.87, 117.25, 113.68, 109.87, 79.58, 69.96, 55.55, 52.41, 51.92, 51.24, 50.92, 50.68, 45.18, 40.52, 38.45, 36.39, 29.76, 29.07, 27.68, 27.58, 23.83, 23.57, 22.54, 22.13, 21.27, 20.53, 14.38, 7.98
HRMS (ESI-TOF)	Calculated for C₅₀H₆₆N₆NaO₉S⁺ [M+Na]⁺: 949.4510, found: 949.4509
[α]25D	+65.0 (c = 0.1, CHCl3)

Compound
Identifier	S43
¹H NMR sample	A mixture of multiple rotamers
¹H NMR (400 MHz, MeOD)	δ 10.05 (s, 1H), 8.40 – 7.94 (m, 6H), 7.48 (s, 1H), 7.29 – 6.98 (m, 5H), 5.03 (s, 2H), 4.57 – 4.40 (m, 5H), 4.26 – 4.06 (m, 2H), 3.69 (s, 3H), 3.24 – 2.89 (m, 2H), 2.69 – 2.43 (m, 2H), 2.08 (s, 3H), 2.07 – 1.95 (m, 2H), 1.72 – 1.56 (m, 9H), 1.44 (s, 9H), 0.93 (d, J = 13.2 Hz, 18H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 172.86, 172.37, 171.72, 155.93, 154.64, 136.22, 132.92, 130.40, 127.26, 126.51, 126.01, 123.35, 121.87, 120.68, 118.02, 117.33, 114.39, 112.19, 108.82, 78.77, 69.43, 55.51, 53.80, 51.75, 51.20, 50.73, 50.24, 39.96, 39.72, 39.28, 30.87, 28.86, 26.80, 23.83, 21.53, 21.46, 20.54, 20.23, 19.89, 13.38
HRMS (ESI-TOF)	Calculated for C₅₃H₇₃BrN₆NaO₉S⁺ [M+Na]⁺: 1071.4241, found: 1071.4238
[α]25D	+17.4 (c = 0.1, CHCl3)
NMR note	Due to the slight impurity, the characterization data were reported after the removal of the acetyl group on indole by the treatment of K2CO3 in methanol

Compound
Identifier	53
¹H NMR sample	A mixture of multiple rotamers
¹H NMR (400 MHz, MeOD)	δ 7.67 (d, J = 7.8 Hz, 1H), 7.49 (d, J = 2.8 Hz, 1H), 7.47 (s, 1H), 7.22 – 7.15 (m, 3H), 7.15 – 7.05 (m, 6H), 5.04 (s, 2H), 4.45 – 4.28 (m, 3H), 3.76 (s, 3H), 3.64 – 3.56 (m, 3H), 3.09 – 3.04 (m, 2H), 2.99 – 2.94 (m, 2H), 2.45 – 2.31 (m, 1H), 2.28 – 2.16 (m, 1H), 2.02 (s, 3H), 1.95 – 1.80 (m, 2H), 1.66 – 1.50 (m, 9H), 1.36 (s, 9H), 0.98 – 0.85 (m, 18H)
¹³C NMR sample	A mixture of multiple rotamers
¹³C NMR (101 MHz, MeOD)	δ 183.04, 178.31, 176.69, 176.42, 171.79, 165.45, 165.38, 161.31, 154.68, 136.19, 132.85, 130.49, 130.36, 127.24, 127.19, 126.50, 125.95, 122.83, 121.73, 117.82, 117.28, 114.48, 112.17, 109.19, 85.76, 77.32, 77.14, 71.63, 70.08, 69.47, 69.36, 69.16, 60.20, 53.36, 51.42, 50.51, 38.80, 38.75, 38.17, 37.23, 34.29, 34.17, 30.76, 28.71, 27.35, 26.98, 26.91, 26.74, 26.61, 25.48, 25.40, 25.16, 23.86, 22.30, 22.24, 18.24, 12.19
HRMS (ESI-TOF)	Calculated for C₅₆H₇₇N₇NaO₁₀S⁺ [M+Na]⁺: 1062.5350, found: 1062.5347
[α]25D	+127.1 (c = 0.02, CHCl3)

Compound
Identifier	56
¹H NMR (600 MHz, CDCl₃)	δ 7.25 – 7.09 (m, 12H), 6.99 (s, 1H), 6.82 (d, J = 8.4 Hz, 3H), 5.22 (d, J = 7.8 Hz, 1H), 4.84 – 4.77 (m, 2H), 4.49 – 4.44 (m, 1H), 4.37 – 4.36 (m, 1H), 4.14 – 4.07 (m, 2H), 3.77 (s, 3H), 3.68 (s, 3H), 3.16 – 3.14 (m, 1H), 3.01 – 2.88 (m, 4H), 2.84 – 2.75 (m, 1H), 1.49 (s, 2H), 1.39 (s, 9H), 0.93 (d, J = 6.0 Hz, 1H), 0.91 (d, J = 8.4 Hz, 1H), 0.82 (t, J = 13.8 Hz, 6H), 0.01 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 171.73, 171.64, 170.97, 170.65, 156.22, 155.78, 150.66, 146.15, 136.46, 131.49, 130.77, 130.70, 129.40, 128.70 (d, J = 7.5 Hz), 128.56, 127.36, 127.02, 126.91, 123.57, 117.82, 117.73, 114.13, 112.53, 80.32, 63.53, 63.44, 56.24, 55.73, 54.01, 52.78, 52.06, 48.73, 41.33, 38.27, 37.19, 36.43, 28.37, 24.72, 24.68, 24.54 (d, J = 15.0 Hz),, 22.95, 22.78, 22.15, 17.31, −1.45
HRMS (ESI-TOF)	Calculated for C₄₆H₆₃BrN₄NaO₁₁Si⁺ [M+Na]⁺: 977.3338, found: 977.3354
[α]25D	+1.0 (c = 0.2, CHCl3)

Compound
Identifier	57
¹H NMR (600 MHz, CDCl₃)	δ 7.23 – 7.15 (m, 7H), 7.10 (d, J = 8.4 Hz, 2H), 7.01 – 6.99 (m, 1H), 6.88 – 6.89 (m, 1H), 6.83 (dd, J = 8.4 Hz, 3H), 6.74 (s, 1H), 6.58 (s, 1H), 5.05 (s, 1H), 4.70 (d, J = 7.8 Hz, 2H), 4.34 (d, J = 48.6 Hz, 2H), 4.20 (d, J = 9.0 Hz, 2H), 3.78 (s, 3H), 3.65 (s, 3H), 3.17 – 3.10 (m, 1H), 3.03 – 2.91 (m, 3H), 2.29 – 2.25 (m, 1H), 2.15 – 2.13 (m, 1H), 1.97 (t, J = 10.8 Hz, 1H), 1.86 (s, 1H), 1.76 (d, J = 14.4 Hz, 1H), 1.37 (s, 9H), 1.31 (s, 4H), 1.29 – 1.28 (m, 2H), 1.24 (s, 5H), 1.06 (d, J = 10.8 Hz, 1H), 0.83 (t, J = 12.6 Hz, 6H), 0.79 (s, 4H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.76, 171.57, 171.45, 170.06, 156.29, 155.79, 150.68, 146.10, 136.66, 131.74, 131.31, 130.69, 130.61, 129.44, 128.79, 128.68, 128.56, 127.41, 127.10, 126.92, 123.63, 117.84, 117.77, 114.13, 112.55, 86.14, 80.53, 56.25, 55.78, 54.18, 52.45, 52.41, 52.14, 51.20, 49.29, 41.18, 39.51, 38.28, 38.19, 37.04, 35.37, 28.59, 28.35, 27.11, 26.32, 24.68, 24.06, 23.01, 22.01
HRMS (ESI-TOF)	Calculated for C₅₀H₆₆BBrN₄NaO₁₁⁺ [M+Na]⁺: 1011.3897, found: 1011.3902
[α]25D	−14.6 (c = 0.2, CHCl3)

Compound
Identifier	58
¹H NMR (600 MHz, CDCl₃)	δ 7.31 (t, J = 15.0 Hz, 3H), 7.22 (s, 1H), 7.11 (dd, J = 24.0 Hz, 4H), 6.95 (d, J = 8.4 Hz, 2H), 6.83 (d, J = 8.4 Hz, 2H), 6.61 (d, J = 8.4 Hz, 2H), 5.99 (d, J = 9.0 Hz, 2H), 5.88 (s, 1H), 5.9 (d, J = 8.4 Hz, 1H), 5.44 (d, J = 7.8 Hz, 2H), 4.89 – 4.87 (m, 1H), 4.37 – 4.31 (m, 2H), 4.23 – 4.19 (m, 1H), 3.85 (s, 3H), 3.64 (s, 3H), 3.11 – 3.04 (m, 3H), 2.86 – 2.79 (m, 2H), 2.64 – 2.60 (m, 1H), 1.43 (s, 9H), 1.15 – 1.14 (m, 2H), 0.98 (d, J = 6.0 Hz, 2H), 0.85 – 0.82 (m, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 170.99, 170.96, 170.49, 169.58, 156.90, 155.54, 155.17, 149.41, 147.05, 135.76, 131.85, 130.38, 129.07, 129.03, 128.73, 128.36, 127.51, 123.87, 120.23, 119.82, 112.51, 107.50, 80.05, 71.48, 56.95, 56.51, 56.12, 52.59, 52.24, 50.68, 41.82, 39.31, 37.34, 37.24, 37.14, 36.80, 28.43, 26.79, 26.77, 26.70, 26.68, 26.19, 26.17, 26.09, 26.06, 25.96, 24.53, 23.10, 22.63, 22.02, 22.00
HRMS (ESI-TOF)	Calculated for C₄₀H₅₀N₄NaO₉⁺ [M+Na]⁺: 753.3470, found: 753.3475
[α]25D	−2.1 (c = 0.2, CHCl3)

Compound
Identifier	59
¹H NMR (600 MHz, CDCl₃)	δ 7.38 – 7.33 (m, 2H), 7.23 – 7.12 (m, 11H), 6.84 – 6.76 (m, 2H), 4.92 – 4.80 (m, 2H), 4.63 – 4.45 (m, 2H), 4.14 – 4.06 (m, 2H), 3.67 (s, 3H), 3.16 – 3.09 (m, 1H), 3.01 – 2.73 (m, 6H), 1.35 (s, 9H), 0.94 – 0.89 (m, 2H), 0.84 – 0.81 (m, 7H), 0.02 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 171.79, 171.74, 171.00, 170.97, 170.71, 156.60, 155.76, 155.67, 155.59, 132.73, 132.70, 130.94, 129.48, 129.44, 128.65, 128.54, 126.95, 126.89, 120.39, 119.10, 63.41, 55.69, 54.01, 52.76, 51.98, 51.85, 48.74, 48.71, 41.77, 41.46, 38.62, 38.40, 38.14, 37.69, 37.52, 36.45, 36.29, 28.40, 28.36, 24.78, 24.72, 22.93, 22.82, 22.34, 22.31, 22.22, 17.46, 17.31, −1.45
HRMS (ESI-TOF)	Calculated for C₄₅H₆₁BrN₄NaO₁₀Si⁺ [M+Na]⁺: 947.3233, found: 947.3238
[α]25D	−19.2 (c = 0.2, CHCl3)

Compound
Identifier	60
¹H NMR (600 MHz, CDCl₃)	δ 7.37 (d, J = 9.0 Hz, 1H), 7.24 – 7.11 (m, 9H), 6.89 – 6.85 (m, 2H), 6.83 – 6.80 (m, 2H), 6.74 – 6.69 (m, 1H), 6.62 – 6.50 (m, 1H), 4.71 – 4.67 (m, 2H), 4.42 – 4.28 (m, 2H), 4.22 – 4.20 (m, 1H), 3.66 (s, 3H), 3.10 – 2.92 (m, 4H), 2.29 – 2.24 (m, 1H), 2.17 – 2.13 (m, 1H), 2.04 – 1.96 (m, 2H), 1.88 – 1.86 (m, 1H), 1.78 – 1.74 (m, 1H), 1.53 – 1.46 (m, 4H), 1.37 (s, 9H), 1.32 – 1.23 (m, 10H), 1.06 (t, J = 20.4 Hz, 1H), 0.85 – 0.79 (m, 10H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.77, 172.72, 171.58, 171.45, 171.39, 169.98, 156.53, 155.76, 136.73, 136.55, 132.74, 131.98, 130.88, 129.47, 129.43, 129.39, 129.32, 128.80, 128.70, 128.59, 127.11, 126.97, 126.93, 120.48, 119.19, 115.71, 86.16, 77.98, 55.79, 54.26, 52.41, 52.14, 52.04, 51.20, 49.31, 49.28, 41.36, 41.09, 39.51, 38.25, 38.20, 37.33, 35.37, 28.58, 28.36, 27.11, 26.32, 24.68, 24.63, 24.06, 23.01, 22.05, 14.74
HRMS (ESI-TOF)	Calculated for C₄₉H₆₄BBrN₄NaO₁₀⁺ [M+Na]⁺: 981.3791, found: 981.3786
[α]25D	−8.1 (c = 0.2, CHCl3)

Compound
Identifier	61
¹H NMR (600 MHz, CDCl₃) sample	A mixture of two rotamers
¹H NMR (600 MHz, CDCl₃) reporting	Signals of the major isomer were reported
¹H NMR (600 MHz, CDCl₃)	δ 7.30 – 7.27 (m, 2H), 7.14 – 7.12 (m, 5H), 6.93 (d, J = 8.4 Hz, 2H), 6.82 – 6.79 (m, 4H), 5.96 (s, 1H), 5.69 – 5.61 (m, 2H), 5.37 (d, J = 7.8 Hz, 1H), 4.65 – 4.62 (m, 1H), 4.39 – 4.35 (m, 1H), 4.23 – 4.17 (m, 2H), 3.76 (s, 9H), 3.31 (dd, J = 14.4 Hz, 1H), 3.11 – 3.09 (m, 1H), 2.98 – 2.90 (m, 2H), 2.86 – 2.81 (m, 1H), 2.75 – 2.71 (m, 1H), 1.44 (s, 9H), 1.37 – 1.35 (m, 2H), 1.15 (d, J = 6.0 Hz, 1H), 0.99 (d, J = 6.0 Hz, 1H), 0.83 – 0.81 (m, 7H)
¹H NMR (400 MHz, CD₃OD)	δ 7.27 – 7.22 (m, 5H), 7.20 (d, J = 8.4 Hz, 2H), 7.04 (d, J = 4.8 Hz, 2H), 6.90 (d, J = 4.4 Hz, 2H), 6.67 (d, J = 8.4 Hz, 2H), 4.72 (dd, J = 12.0 Hz, 1H), 4.44 (dd, J = 8.0 Hz, 1H), 4.30 (dd, J = 10.4 Hz, 1H), 4.14 (dd, J = 11.2 Hz, 1H), 3.82 (s, 3H), 3.38 (dd, J = 10.0 Hz, 1H), 3.33 (m, 3H), 3.18 (dd, J = 9.6 Hz, 1H), 2.99 – 2.92 (m, 2H), 2.86 – 2.79 (m, 2H), 1.44 (s, 9H), 0.83 (dd, J = 19.2 Hz, 6H)
¹H NMR (400 MHz, CD₃OD, 55 °C)	δ 7.27 – 7.22 (m, 5H), 7.17 (d, J = 8.4 Hz, 2H), 7.06 (d, J = 4.8 Hz, 2H), 6.90 (d, J = 4.4 Hz, 2H), 6.72 (d, J = 8.4 Hz, 2H), 4.71 (dd, J = 12.0 Hz, 1H), 4.40 (dd, J = 8.0 Hz, 1H), 4.31 (dd, J = 10.4 Hz, 1H), 4.13 (dd, J = 11.2 Hz, 1H), 3.82 (s, 3H), 3.35 (m, 1H), 3.33 (m, 3H), 3.15 (dd, J = 9.6 Hz, 1H), 2.99 – 2.92 (m, 2H), 2.87 – 2.79 (m, 2H), 1.45 (s, 9H), 0.82 (dd, J = 19.2 Hz, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 171.78, 170.72, 170.39, 170.29, 158.34, 158.24, 156.94, 155.42, 135.91, 132.75, 131.65, 130.83, 130.48, 130.20, 129.25, 128.87, 127.37, 120.99, 120.66, 107.55, 80.28, 71.51, 56.42, 54.84, 53.01, 52.74, 51.36, 42.25, 38.42, 38.21, 37.98, 37.28, 36.92, 28.43, 26.81, 26.72, 26.22, 26.14, 25.99, 24.66, 24.08, 23.16, 22.64, 22.01, 21.77
HRMS (ESI-TOF)	Calculated for C₃₉H₄₈N₄NaO₈⁺ [M+Na]⁺: 723.3364, found: 753.3373
[α]25D	−6.5 (c = 0.2, CHCl3)
NMR note	Due to the rotamerism, ¹H NMR was recorded at 55 °C in CD₃OD. However, even at the elevated temperature, the rotamerism was not partially resolved

Compound
Identifier	63
¹H NMR (600 MHz, CDCl₃)	δ 7.32 (s, 1H), 7.20 (d, J = 10.8 Hz, 1H), 7.13 (d, J = 8.4 Hz, 2H), 7.02 – 6.99 (m, 1H), 6.88 – 6.84 (m, 3H), 4.90 – 4.88 (m, 1H), 4.69 (s, 1H), 4.35 – 4.28 (m, 2H), 4.15 (t, J = 7.2 Hz, 2H), 3.80 (s, 3H), 3.72 (s, 3H), 3.08 (d, J = 16.8 Hz, 1H), 2.99 – 2.96 (m, 2H), 2.80 – 2.78 (m, 1H), 2.57 – 2.54 (m, 2H), 2.14 – 2.06 (m, 6H), 1.99 – 1.95 (m, 1H), 1.38 (s, 9H), 0.97 – 0.94 (m, 2H), 0.87 (d, J = 17.1 Hz, 6H), 0.00 (s, 9H)
¹³C NMR (151 MHz, CDCl₃)	δ 171.97, 171.17, 171.00, 170.86, 170.74, 156.28, 155.93, 150.63, 146.18, 131.28, 131.24, 130.66, 130.61, 130.44, 127.36, 123.50, 118.04, 117.94, 117.53, 114.11, 112.55, 80.69, 63.68, 63.56, 58.84, 58.61, 56.26, 56.10, 52.88, 52.83, 52.07, 48.67, 48.58, 36.97, 36.42, 36.35, 31.50, 30.60, 29.98, 29.78, 28.35, 19.35, 17.86, 17.35, 17.32, 15.35, 15.18, 15.05, −1.28, −1.45, −1.62
HRMS (ESI-TOF)	Calculated for C₄₁H₆₁BrN₄NaO₁₁Si⁺ [M+Na]⁺: 947.2902, found: 947.2914
[α]25D	+59.8 (c = 0.1, CHCl3)

Compound
Identifier	64
¹H NMR (600 MHz, CDCl₃)	δ 7.18 (dd, J = 7.2 Hz, 1H), 7.13 – 7.11 (m, 2H), 7.01 (d, J = 2.4 Hz, 1H), 6.86 – 6.83 (m, 3H), 4.76 – 4.73 (m, 1H), 4.68 – 4.64 (m, 1H), 4.37 – 4.30 (m, 2H), 4.25 – 4.24 (m, 1H), 3.79 (s, 3H), 3.67 (s, 3H), 3.08 – 2.94 (m, 2H), 2.56 – 2.54 (m, 2H), 2.31 – 2.26 (m, 1H), 2.18 – 2.05 (m, 8H), 1.99 (t, J = 4.8 Hz, 1H), 1.96 – 1.93 (m, 1H), 1.88 – 1.86 (m, 1H), 1.82 – 1.79 (m, 1H), 1.37 (s, 9H), 1.34 (s, 3H), 1.25 (s, 3H), 1.08 (d, J = 10.8 Hz, 1H), 0.86 (dd, J = 18.6 Hz, 1H), 0.80 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.90, 171.77, 170.65, 170.46, 156.23, 155.86, 150.62, 146.22, 131.69, 131.36, 130.69, 130.64, 127.32, 123.48, 117.99, 114.11, 112.55, 86.34, 86.27, 80.55, 78.07, 58.72, 56.26, 56.04, 52.43, 52.02, 51.21, 49.24, 49.11, 39.53, 38.21, 37.09, 35.36, 31.65, 30.86, 29.90, 28.63, 28.36, 27.11, 26.34, 24.06, 19.34, 17.92, 15.02, 14.49, 0.08
HRMS (ESI-TOF)	Calculated for C₄₅H₆₄BBrN₄NaO₁₁S⁺ [M+Na]⁺: 981.3461, found: 981.3461
[α]25D	+10.6 (c = 0.1, CHCl3)

Compound
Identifier	65
¹H NMR (600 MHz, CDCl₃)	δ 7.28 (s, 1H), 7.15 (d, J = 8.4 Hz, 2H), 7.01 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz, 1H), 6.62 (d, J = 8.4 Hz, 2H), 6.30 – 6.28 (m, 1H), 5.79 (s, 1H), 5.63 (s, 1H), 4.94 (s, 1H), 4.31 (s, 1H), 4.26 – 4.24 (m, 1H), 3.93 (s, 1H), 3.88 (s, 3H), 3.70 (s, 3H), 3.17 – 3.08 (m, 2H), 2.79 – 2.76 (m, 1H), 2.67 (t, J = 10.8 Hz, 1H), 2.65 – 2.50 (m, 2H), 2.07 (s, 3H), 2.01 – 1.98 (m, 1H), 1.93 – 1.89 (m, 2H), 1.43 (s, 9H), 0.83 (dd, J = 29.4 Hz, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 171.20, 170.87, 170.14, 169.73, 155.30, 155.24, 149.27, 147.61, 145.59, 132.14, 130.59, 130.36, 128.29, 123.55, 121.27, 121.24, 120.92, 119.27, 112.49, 80.43, 79.99, 57.14, 56.65, 56.14, 54.64, 52.42, 52.29, 39.60, 38.20, 37.37, 31.83, 30.19, 29.76, 29.67, 28.61, 28.46, 28.35, 19.01, 18.44, 17.64, 15.47, 0.08
HRMS (ESI-TOF)	Calculated for C₃₅H₄₈N₄NaO₉S⁺ [M+Na]⁺: 723.3034, found: 723.3032
[α]25D	+62.2 (c = 0.1, CHCl3)

Compound
Identifier	68
¹H NMR (600 MHz, CDCl₃)	δ 8.59 – 8.55 (m, 3H), 8.42 – 8.41 (m, 1H), 8.30 (s, 1H), 7.86 (s, 2H), 7.77 – 7.70 (m, 3H), 7.56 – 7.54 (m, 1H), 7.32 – 7.27 (m, 4H), 7.15 (s, 1H), 7.07 (d, J = 8.4 Hz, 3H), 7.02 (s, 1H), 6.86 – 6.82 (m, 3H), 6.63 (s, 1H), 5.15 (s, 1H), 4.88 (s, 1H), 4.78 (s, 1H), 4.66 – 4.44 (m, 5H), 3.95 (s, 1H), 3.75 (s, 3H), 3.68 (s, 3H), 3.51 – 3.40 (m, 2H), 3.28 – 3.26 (m, 1H), 3.16 – 3.11 (m, 5H), 2.97 – 2.94 (m, 1H), 2.65 (s, 5H), 2.29 – 2.13 (m, 6H), 1.98 – 1.96 (m, 8H), 1.49 (s, 9H), 1.46 (s, 9H), 1.39 (s, 9H), 1.23 (s, 1H), 0.96 – 0.90 (m, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 172.32, 171.96, 170.93, 170.50, 169.82, 163.48, 156.29, 155.55, 154.28, 153.38, 148.39, 148.22, 147.13, 146.53, 144.31, 144.03, 140.34, 139.13, 137.29, 137.07, 136.20, 135.11, 135.05, 130.81, 129.51, 129.31, 128.87, 128.60, 128.21, 127.72, 123.98, 123.33, 122.21, 121.97, 121.68, 121.25, 119.91, 118.08, 117.42, 112.92, 111.88, 83.73, 80.99, 80.08, 56.57, 56.30, 55.67, 54.71, 53.53, 52.68, 52.43, 51.27, 40.54, 36.30, 30.51, 30.38, 29.88, 29.78, 29.07, 28.58, 28.35, 28.29, 28.17, 18.84, 18.51, 15.54, 14.99, 0.08
HRMS (ESI-TOF)	Calculated for C₉₁H₁₁₃N₂₁NaO₂₆S₂⁺ [M+Na]⁺: 2002.7499, found: 2002.7394
[α]25D	−1.4 (c = 0.1, CHCl3)