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JZ9.2 Hz, 1H), 5.98–6.02 (m, 1H), 7.26–7.29 (m, 2H),
7.36–7.39 (m, 3H), 7.58 (dd, JZ7.5, 12.7 Hz, 2H), 7.61 (d,
JZ9.7 Hz, 1H), 7.75 (d, JZ7.5 Hz, 2H), 8.06 (s, 1H), 8.10
(s, 1H); 13C NMR (150 MHz, CDCl3) d 11.6, 17.9, 18.0,
18.3, 18.8, 18.9, 19.5, 32.2 (2C), 32.9, 47.1, 52.1, 54.7, 56.0,
65.8, 66.8, 118.7, 119.9, 124.8 (2C), 126.9, 127.2, 127.6,
128.4, 131.7, 135.4, 141.2 (2C), 141.4, 143.5, 143.7, 146.9,
153.6, 155.9, 160.2, 160.4, 160.7, 161.4, 163.1, 171.4;
HRMS (MALDI-FTMS) calcd for C43H48N6O8S (MCHC)
809.3327, found 809.3318.
d6) d 12.2, 18.9, 19.0, 19.1, 19.2, 19.4, 33.7, 35.3, 35.5, 53.2,
55.5, 55.7, 125.7, 126.2, 128.7, 148.7, 149.2, 154.2, 159.9,
160.4, 160.6, 161.4, 169.4, 169.9; HRMS (MALDI-FTMS)
calcd for C25H32N6O4S2 (MCNaC) 567.1819, found
567.1810.
4.1.15. Compound 23. Compound 23 was synthesized from
19 and N-Fmoc-O-trityl-threonine in a 94% yield as a white
foam by following the procedure used for the synthesis of
1
12: [a]2D4ZK15.0 (c 0.50, CHCl3); H NMR (600 MHz,
CDCl3, 25 8C, TMS) d 0.80 (d, JZ7.0 Hz, 3H), 0.88 (d, JZ
6.6 Hz, 3H), 0.97 (d, JZ6.6 Hz, 3H), 1.00 (d, JZ7.0 Hz,
3H), 1.17 (d, JZ6.1 Hz, 3H), 2.21–2.27 (m, 1H), 2.56–2.62
(m, 1H), 3.44 (br, 1H), 4.13 (t, JZ7.5 Hz, 1H), 4.22–4.29
(m, 2H), 4.35 (br, 1H), 4.82 (d, JZ5.7 Hz, 2H), 5.08 (dd,
JZ8.8, 6.6 Hz, 1H), 5.26 (d, JZ10.5 Hz, 1H), 5.37 (d, JZ
17.1 Hz, 1H), 5.41 (dd, JZ8.8, 6.6 Hz, 1H), 5.73 (d, JZ
4.8 Hz, 1H), 5.97–6.02 (m, 1H), 7.23–7.30 (m, 12H), 7.35–
7.38 (m, 2H), 7.52–7.57 (m, 9H), 7.72–7.74 (m, 2H), 8.09
(s, 1H), 8.22 (s, 1H); 13C NMR (150 MHz, CDCl3) d 16.1,
17.6, 18.2, 19.0, 19.5, 31.8, 33.0, 47.0, 53.1, 56.1, 65.9,
66.7, 69.8, 88.6, 118.9, 119.9, 125.0, 125.1, 126.9 (2C),
127.2, 127.5, 127.6, 128.2, 128.7, 131.8, 135.6, 141.2,
141.6, 143.7 (d), 147.2, 155.0, 160.3, 160.8, 163.7, 169.6,
171.9; HRMS (MALDI-FTMS) calcd for C57H57N5O8S
(MCNaC) 994.382, found 994.3805.
4.1.12. Bistratamide G (3). Compound 3 was synthesized
from 20 in a 70% yield as a white solid by following the
procedure used for the synthesis of 2: mp 224–226 8C;
[a]D24ZK84.4 (c 0.97, MeOH) {lit4c [a]2D5ZK73.8 (c 1.0,
MeOH)}; 1H NMR (600 MHz, DMSO-d6, 25 8C) d 0.88 (d,
JZ6.6 Hz, 3H), 0.91 (d, JZ6.6 Hz, 3H), 0.93 (d, JZ
7.0 Hz, 3H), 0.94 (d, JZ7.0 Hz, 3H), 0.96 (d, JZ6.6 Hz,
3H), 0.97 (d, JZ7.0 Hz, 3H), 2.15–2.22 (m, 2H), 2.27–2.31
(m, 1H), 2.54 (s, 3H), 5.01 (dd, JZ4.4, 7.5 Hz, 1H), 5.09
(dd, JZ5.7, 8.8 Hz, 1H), 5.39 (dd, JZ6.1, 8.8 Hz, 1H), 8.30
(d, JZ7.0 Hz, 1H), 8.32 (d, JZ9.2 Hz, 1H), 8.35 (s, 1H),
8.44 (d, JZ8.8 Hz, 1H), 8.78 (s, 1H); 13C NMR (150 MHz,
DMSO-d6) d 11.1, 18.0, 18.1, 18.2, 18.3, 18.6, 32.6, 32.9,
34.6, 52.1, 52.7, 54.8, 125.2, 128.0, 134.5, 142.9, 147.9,
152.8, 158.4, 159.3, 160.2, 160.5, 163.2, 168.3; HRMS
(MALDI-FTMS) calcd for C25H32N6O5S (MCHC)
529.2228, found 529.2221.
4.1.16. Compound 24. Compound 24 was synthesized from
23 in a 92% yield as a white foam by following the
procedure used for the synthesis of 12: [a]2D4ZK25.6 (c
4.1.13. Compound 22. Compound 22 was synthesized from
21 and 17 in a 97% yield as a white foam by following the
procedure used for the synthesis of 12: [a]2D4ZK27.1 (c
1
1.21, CHCl3); H NMR (600 MHz, CDCl3, 25 8C, TMS) d
0.79 (d, JZ6.6 Hz, 3H), 0.84 (d, JZ6.6 Hz, 3H), 0.87 (d,
JZ6.6 Hz, 3H), 0.88 (d, JZ6.6 Hz, 3H), 0.94 (d, JZ
6.6 Hz, 3H), 0.98 (d, JZ6.6 Hz, 3H), 1.13 (d, JZ6.1 Hz,
3H), 2.04–2.06 (m, 1H), 2.20–2.22 (m, 1H), 2.55–2.58 (m,
1H), 3.62 (br, 1H), 4.01 (t, JZ6.1 Hz, 1H), 4.19 (m, 1H),
4.32 (dd, JZ10.5, 7.0 Hz, 1H), 4.37–4.42 (m, 2H), 4.82 (d,
JZ5.7 Hz, 2H), 5.04 (dd, JZ8.3, 6.6 Hz, 1H), 5.26 (d, JZ
10.5 Hz, 1H), 5.37 (d, JZ17.1 Hz, 1H), 5.40 (dd, JZ9.2,
6.1 Hz, 1H), 5.45 (d, JZ8.8 Hz, 1H), 5.96–6.01 (m, 1H),
6.81 (d, JZ4.8 Hz, 1H), 7.22–7.29 (m, 11H), 7.38 (t, JZ
7.0 Hz, 2H), 7.54–7.58 (m, 10H), 7.60 (d, JZ9.2 Hz, 1H),
7.75 (d, JZ7.5 Hz, 1H), 8.07 (s, 1H), 8.20 (s, 1H); 13C
NMR (150 MHz, CDCl3) d 16.3, 17.5, 17.6, 18.2, 18.9,
19.1, 19.5, 31.3, 31.7, 33.0, 47.1, 53.2, 55.4, 56.0, 60.0,
65.9, 66.9, 69.2, 88.6, 118.8, 119.9, 125.0, 127.0, 127.2,
127.5, 127.6, 128.1, 128.7, 131.8, 135.5, 141.2, 141.6,
143.6, 143.7, 143.9, 147.1, 156.2, 160.3, 160.8, 163.6,
169.5, 170.2, 171.8; HRMS (MALDI-FTMS) calcd for
C62H66N6O9S (MCNaC) 1093.4504, found 1093.4547.
1
0.77, CHCl3); H NMR (600 MHz, CDCl3, 25 8C, TMS) d
0.94 (d, JZ6.6 Hz, 3H), 0.97 (d, JZ7.0 Hz, 3H), 1.00 (d,
JZ7.0 Hz, 3H), 1.03 (d, JZ7.5 Hz, 6H), 1.05 (d, JZ
7.9 Hz, 3H), 2.20–2.23 (m, 1H), 2.52–2.55 (m, 1H), 2.62–
2.65 (m, 1H), 2.63 (s, 3H), 4.21 (dd, JZ6.6, 7.0 Hz, 1H),
4.40–4.49 (m, 2H), 4.77 (dd, JZ6.6, 9.2 Hz, 1H), 4.83 (m,
2H), 5.28 (d, JZ10.1 Hz, 1H), 5.31 (dd, JZ6.1, 9.2 Hz,
1H), 5.34 (dd, JZ6.6, 9.2 Hz, 1H), 5.39 (d, JZ17.1 Hz,
1H), 5.45 (m, 1H), 5.99–6.04 (m, 1H), 7.24–7.28 (m, 2H),
7.37 (t, JZ7.5 Hz, 2H), 7.46 (d, JZ8.8 Hz, 1H), 7.57 (dd,
JZ7.9, 8.3 Hz, 2H), 7.75 (d, JZ7.5 Hz, 2H), 7.99 (d, JZ
9.2 Hz, 1H), 8.01 (s, 1H), 8.06 (s, 1H); 13C NMR (150 MHz,
CDCl3) d 11.7, 17.8 (2C), 18.0, 18.9, 19.4, 19.6, 32.3, 32.8,
33.0, 47.1, 54.7, 55.8, 56.4, 65.8, 66.8, 118.7, 119.9, 123.5,
124.8, 124.9, 126.9, 127.2, 127.7, 128.4, 131.8, 141.2 (2C),
143.5, 143.7, 147.0, 149.3, 153.7, 155.9, 160.5, 160.7,
160.8, 161.6, 171.8, 171.9; HRMS (MALDI-FTMS)
calcd for C43H48N6O7S2 (MCHC) 825.3098, found
825.3084.
4.1.17. Compound 25. Compound 25 was synthesized from
24 in a 85% yield as a white foam by following the
procedure used for the synthesis of 2: [a]2D4ZK115.5 (c
4.1.14. Bistratamide H (4). Compound 4 was synthesized
from 22 in a 80% yield as a gel-like solid by following the
procedure used for the synthesis of 2: [a]2D4ZK106.2 (c 1.1,
MeOH) {lit4c [a]D25ZK92.9 (c 1.0, MeOH)}; 1H NMR
(600 MHz, DMSO-d6, 25 8C) d 0.90 (d, JZ6.6 Hz, 3H),
0.93 (d, JZ7.0 Hz, 6H), 0.94 (d, JZ8.3 Hz, 3H), 0.96 (d,
JZ7.0 Hz, 3H), 0.98 (d, JZ7.0 Hz, 3H), 2.16–2.25 (m, 3H),
2.58 (s, 3H), 5.07 (dd, JZ5.3, 8.3 Hz, 1H), 5.35 (dd, JZ5.3,
8.3 Hz, 1H), 5.45 (dd, JZ7.0, 9.6 Hz, 1H), 8.33 (s, 1H),
8.35 (s, 1H), 8.36 (d, JZ9.2 Hz, 1H), 8.49 (d, JZ8.3 Hz,
1H), 8.52 (d, JZ9.7 Hz, 1H); 13C NMR (150 MHz, DMSO-
1
0.27, CHCl3); H NMR (600 MHz, CDCl3, 25 8C, TMS) d
0.75 (d, JZ6.6 Hz, 3H), 0.90 (d, JZ7.0 Hz, 3H), 0.92 (d,
JZ6.6 Hz, 3H), 0.98 (d, JZ6.6 Hz, 3H), 1.00 (d, JZ
7.0 Hz, 3H), 1.09 (d, JZ7.0 Hz, 3H), 1.46 (d, JZ6.6 Hz,
3H), 2.17–2.22 (m, 1H), 2.35–2.38 (m, 1H), 2.54–2.56 (m,
1H), 3.65 (dd, JZ5.3, 4.4 Hz, 1H), 4.53–4.55 (m, 1H), 4.63
(dd, JZ10.5, 3.5 Hz, 1H), 4.76 (dd, JZ6.1, 4.4 Hz, 1H),
5.22 (dd, JZ9.7, 7.0 Hz, 1H), 6.84 (d, JZ5.3 Hz, 1H),
7.26–7.29 (m, 3H), 7.33–7.35 (m, 6H), 7.45 (d, JZ10.1 Hz,