8482
F. Xue, C. T. Seto / Bioorg. Med. Chem. 14 (2006) 8467–8487
4H), 1.41–1.55 (m, 13H), 2.50–2.65 (dd, J = 4.0, 8.0 Hz,
2H), 2.85–3.35 (m, 5H), 3.36–3.55 (m, 2H), 4.25–4.70
(m, 2H); 13C NMR (100 MHz, CDCl3) d ꢀ0.1, 0.0,
26.5, 26.6, 26.8, 26.9, 28.4, 30.0, 30.1, 40.5, 47.2, 48.0,
54.1, 55.6, 58.0, 59.9, 60.1, 62.7, 70.0, 72.6, 79.1, 156.0;
HRMS-FAB (M+Na+) calcd for C18H38NaN2O5SSi
445.2168, found 445.2145.
208.2, 208.3; HRMS-FAB (M+Na+) calcd for
C48H61NaN5O10 890.4316, found 890.4334.
4.3.10.49. Ketone 20d. Compound 20d was synthe-
sized starting from 19d using general method H
(50 mg, 57 mmol, 65%): H NMR (400 MHz, CDCl3)
1
d 1.00–1.35 (m, 10H), 1.40–1.55 (m, 12H), 1.56–1.70
(m, 9H), 2.50–2.85 (m, 2H), 2.86–3.30 (m, 7H), 3.40–
3.55 (m, 1H), 3.85–4.05 (m, 2H), 4.06–4.30 (m, 2H),
4.35–4.60 (m, 1H), 4.62–4.80 (m, 1H), 4.81–5.05 (m,
1H), 5.05–5.20 (m, 2H), 5.25–5.65 (m, 1H), 6.30–6.80
(m, 1H), 6.96–7.27 (m, 7H), 7.30–7.42 (m, 6H), 7.43–
7.54 (m, 1H), 7.55–7.70 (m, 1H), 8.05–8.20 (m, 1H);
13C NMR (100 MHz, CDCl3) d 26.0, 26.5, 28.1, 28.4,
28.6, 29.1, 29.8, 39.2, 39.5, 40.4, 50.0, 50.1, 54.9, 61.7,
61.8, 61.9, 66.9, 67.1, 67.7, 67.8, 69.5, 79.0, 83.6, 83.7,
115.3, 115.5, 119.0, 122.7, 122.8, 124.2, 124.3, 124.6,
124.7, 127.0, 127.1, 127.2, 128.1, 128.2, 128.5, 128.6,
129.3, 129.4, 129.7, 135.2, 135.3, 135.5, 135.7, 136.0,
149.4, 155.8, 156.0, 169.5, 169.8, 169.9, 170.0, 207.6,
207.7; HRMS-FAB (M+Na+) calcd for C49H63Na-
N5O10 904.4473, found 904.4450.
4.3.10.46. Ketone 20a. Compound 20a was synthe-
sized starting from 19a using general method H
1
(41 mg, 49 lmol, 81%): H NMR (300 MHz, CDCl3) d
1.10–1.37 (m, 4H), 1.38–1.52 (m, 10H), 1.53–1.72 (m,
9H), 2.50–3.30 (m, 8H), 3.35–3.60 (m, 1H), 3.85–4.25
(m, 4H), 4.30–4.60 (m, 1H), 4.75–5.04 (m, 2H), 5.05–
5.20 (m, 2H), 5.20–5.70 (m, 1H), 6.25–6.75 (m, 1H),
6.95–7.17 (m, 2H), 7.18–7.26 (m, 3H), 7.28–7.40 (m,
6H), 7.41–7.51 (m, 1H), 7.55–7.70 (m, 1H), 8.00–8.20
(m, 1H); 13C NMR (75 MHz, CDCl3) d 26.5, 26.7,
26.8, 27.0, 28.2, 28.5, 28.6, 28.8, 39.5, 39.7, 39.9, 49.9,
50.1, 50.4, 55.4, 55.7, 62.1, 62.3, 67.3, 67.4, 67.6, 68.0,
68.2, 70.0, 79.7, 84.1, 84.3, 84.4, 115.4, 115.8, 119.4,
123.2, 124.7, 124.8, 124.9, 125.0, 125.2, 127.6, 127.7,
128.5, 128.6, 128.7, 128.8, 128.9, 129.0, 129.8, 129.9,
130.2, 130.5, 135.6, 135.7, 135.8, 135.9, 136.1, 136.4,
149.9, 150.0, 156.2, 156.5, 170.0, 170.1, 170.3, 170.4,
170.6, 208.1, 208.2; HRMS-ESI (M+Na+) calcd for
C46H57NaN5O10 862.4003, found 862.4025.
4.3.10.50. Ketone 20e. Compound 20e was synthe-
sized starting from 19e using general method H
1
(40 mg, 46 lmol, 52%): H NMR (300 MHz, CDCl3) d
1.40–1.55 (m, 9H), 1.56–1.70 (m, 9H), 2.55–3.10 (m,
2H), 3.11–3.27 (m, 2H), 3.30–3.50 (m, 1H), 3.65–3.5
(m, 3H), 4.05–4.20 (m, 1H), 4.25–4.65 (m, 2H), 4.90–
5.25 (m, 3H), 5.25–5.65 (m, 1H), 6.40–6.95 (m, 3H),
7.00–7.08 (m, 1H), 7.09–7.20 (m, 2H), 7.21–7.30 (m,
3H), 7.31–7.42 (m, 7H), 7.43–7.70 (m, 2H), 8.00–8.15
(m, 1H); 13C NMR (75 MHz, CDCl3) d 14.6, 28.2,
28.6, 28.7, 29.4, 50.4, 50.7, 53.1, 53.2, 61.1, 61.3, 61.6,
67.5, 67.6, 67.8, 68.0, 70.0, 77.7, 81.2, 84.1, 84.2, 84.3,
115.6, 115.7, 115.8, 119.2, 119.3, 119.5, 123.1, 123.2,
124.7, 124.8, 124.9, 125.1, 127.6, 127.7, 128.5, 128.6,
128.7, 128.9, 129.0, 129.1, 129.2, 129.6, 129.8, 130.0,
130.1, 130.2, 131.7, 135.4, 135.8, 136.1, 136.5, 138.8,
139.0, 149.9, 153.0, 156.3, 170.3, 170.5, 170.6, 170.7,
170.8, 208.3, 208.4; HRMS-ESI (M+Na+) calcd for
C49H55NaN5O10 896.3847, found 896.3862.
4.3.10.47. Ketone 20b. Compound 20b was synthesized
starting from 19b using general method H (47 mg,
1
55 lmol, 62%): H NMR (300 MHz, CDCl3) d 1.00–
1.30 (m, 3H), 1.31–1.51 (m, 11H), 1.52–1.70 (m, 9H),
2.50–3.30 (m, 8H), 3.33–3.50 (m, 1H), 3.85–4.06 (m,
2H), 4.07–4.30 (m, 2H), 4.35–4.60 (m, 1H), 4.62–5.04
(m, 2H), 5.05–5.15 (m, 2H), 5.20–5.70 (m, 1H), 6.25–
6.80 (m, 1H), 6.95–7.17 (m, 2H), 7.19–7.27 (m, 3H),
7.29–7.33 (m, 6H), 7.34–7.51 (m, 1H), 7.50–7.70 (m,
1H), 8.00–8.20 (m, 1H); 13C NMR (75 MHz, CDCl3) d
23.7, 28.5, 28.6, 28.8, 29.1, 29.2, 29.3, 29.9, 39.6, 40.5,
50.3, 50.4, 50.5, 62.1, 62.2, 67.4, 67.5, 67.7, 68.1, 70.0,
77.7, 84.1, 84.3, 115.8, 119.4, 119.5, 123.1, 123.2, 124.7,
124.8, 124.9, 125.1, 125.2, 127.5, 127.6, 127.7, 128.5,
128.6, 128.7, 129.0, 129.8, 129.9, 130.2, 135.7, 135.9,
136.5, 170.3, 170.6, 208.1, 208.2; HRMS-ESI (M+Na+)
calcd for C47H59NaN5O10 876.4160, found 876.4176.
4.3.10.51. Ketone 20f. Compound 20f was synthesized
starting from 19f using general method H (43 mg,
1
49 lmol, 56%): H NMR (300 MHz, CDCl3) d 0.70–
4.3.10.48. Ketone 20c. Compound 20c was synthe-
sized starting from 19c using general method H
(51 mg, 59 lmol, 66%): H NMR (300 MHz, CDCl3) d
1.10 (m, 5H), 1.11–1.31 (m, 1H), 1.35–1.55 (m, 10H),
1.56–1.70 (m, 9H), 1.80–2.00 (m, 2H), 2.45–3.25 (m,
6H), 3.26–3.55 (m, 2H), 3.90–4.28 (m, 4H), 4.29–4.40
(m, 1H), 4.41–4.55 (m, 1H), 4.75–5.02 (m, 1H), 5.03–
5.13 (m, 2H), 5.20–5.60 (m, 1H), 6.20–6.70 (m, 1H),
6.95–7.16 (m, 2H), 7.17–7.28 (m, 4H), 7.30–7.42 (m,
6H), 7.43–7.53 (m, 1H), 7.55–7.74 (m, 1H), 8.00–8.20
(m, 1H); 13C NMR (75 MHz, CDCl3) d 28.5, 28.6,
28.8, 29.1, 29.2, 29.4, 33.0, 33.1, 37.8, 39.5, 39.9, 49.8,
50.5, 52.2, 56.1, 63.1, 67.1, 67.3, 67.6, 67.8, 67.9, 70.0,
70.1, 77.7, 79.6, 84.1, 84.3, 115.5, 115.7, 115.8, 119.5,
123.2, 123.3, 124.7, 125.0, 125.2, 127.5, 127.6, 127.7,
128.5, 128.7, 129.0, 129.8, 129.9, 130.2, 130.5, 135.7,
135.9, 136.2, 136.4, 149.9, 155.5, 156.2, 170.3, 170.4,
170.6, 170.7, 170.8, 207.9, 208.0, 208.1, 208.3; HRMS-
ESI (M+Na+) calcd for C49H61NaN5O10 902.4316,
found 902.4301.
1
1.00–1.35 (m, 7H), 1.36–1.52 (m, 9H), 1.53–1.70 (m,
9H), 2.50–3.30 (m, 8H), 3.30–3.50 (m, 1H), 3.85–4.25
(m, 4H), 4.35–4.65 (m, 1H), 4.66–5.02 (m, 2H), 5.03–
5.15 (m, 2H), 5.30–5.70 (m, 1H), 6.40–6.80 (m, 1H),
6.97–7.17 (m, 2H), 7.18–7.27 (m, 4H), 7.29–7.40 (m,
6H), 7.41–7.49 (m, 1H), 7.50–7.65 (m, 1H), 8.00–8.20
(m, 1H); 13C NMR (75 MHz, CDCl3) d 26.1, 26.5,
28.3, 28.6, 28.9, 29.4, 29.6, 30.1, 39.6, 39.9, 40.7, 50.3,
50.4, 50.5, 55.3, 62.2, 62.3, 67.4, 67.5, 68.1, 68.2, 70.0,
77.7, 79.5, 84.2, 84.3, 115.5, 115.6, 115.7, 119.4, 123.1,
123.2, 124.7, 124.8, 125.0, 125.1, 127.5, 127.6, 127.7,
128.5, 128.6, 128.9, 129.8, 129.9, 130.2, 130.5, 130.6,
135.7, 135.8, 136.0, 136.2, 136.5, 149.9, 156.2, 156.5,
170.0, 170.1, 170.3, 170.4, 170.5, 170.6, 208.0, 208.1,