352
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125.8, 128.3, 128.7, 133.3, 133.7, 137.7, 162.5, 166.5, 166.8,
167.1, 168.4, 199.2. HRMS (FAB, DCM/NBA/NaCl) m/z
calcd for C43H53NO14Na+ 832.3364, found 832.3369
(ꢀ=À0.6 ppm).
14. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
15. Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.;
Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985.
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20
26. 1(H)a: mp 182–184 ꢀC; ½aꢁD À33.3ꢀ (c 0.12, CHCl3); 1H
NMR (250 MHz, CDCl3) d 0.86 (m, 6H), 1.13 (s, 3H), 1.25 (m,
5H), 1.29 (s, 3H), 1.59 (s, 3H), 1.69 (s, 3H), 1.78 (s, 3H), 2.02
(m, 2H), 2.24, (s, 3H), 2.30 (m, 2H), 2.37 (s, 3H), 2.44 (s, 3H),
2.80 (m, 1H), 3.80 (d, J=7.7 Hz, 1H), 4.24 (m, 2H), 4.47 (b,
1H), 4.81 (b, 1H), 4.90 (d, J=9.3 Hz 1H), 5.14 (b, 1H), 5.35
(d, J=5.4 Hz, 1H), 5.63 (d, J=7.7 Hz, 1H), 6.26, (m, 2H),
7.38 (b, 2H), 7.89 (s, 1H), 8.17 (s, 1H). 13C NMR (62.9 MHz,
CDCl3) d 5.4, 9.6, 10.1, 14.2, 16.3, 18.2, 18.4, 21.3, 22.4, 24.6,
24.8, 25.2, 26.7, 27.4, 30.8, 30.8, 40.9, 47.2, 53.2, 53.8, 58.3,
67.4, 67.8, 70.9, 80.1, 115.0, 123.77, 124.4, 124.9, 126.0, 129.6,
135.5, 137.8, 149.2, 162.0, 165.8, 166.8, 170.2, 199.1. HRMS
(FAB, DCM/NBA/NaCl) m/z calcd for C42H55NO15Na+
832.3156, found 832.3131 (ꢀ=3.1 ppm).
27. Boge, T. C.; Wu, Z.-J.; Himes, R. H.; Vander, D. G.;
Georg, G. I. Bioorg. Med. Chem. Lett. 1999, 9, 3047.
28. Skehan, P.; Streng, R.; Scudierok, D.; Monks, A.;
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MEDI65.
32. Li, Y.; Poliks, B.; Cegelski, L.; Poliks, M.; Cryczynski, A.;
Piszcek, G.; Jagtap, P. G.; Studelska, D. R.; Kingston, D. G. I.;
Schaefer, J.; Bane, S. Biochemistry 2000, 39, 281.
33. Ojima, I., Inoue, T., Slater, J. C., Lin, S., Kuduk, S. C.,
Chakravarty, S., Walsh, J. J., Gilchrist, L., McDermott, A. E.,
Cresteil, T., Monsarrat, B., Pera, P., Bernacki, R. J. In
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and Future Directions, Ramachandran, Ed.; ACS Symp. Ser.
746; American Chemical Society: Washington, DC, 1999;
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24. Ojima, I.; Slater, J. S.; Kuduk, S. D.; Takeuchi, C. S.;
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Bernacki, R. J. J. Med. Chem. 1997, 40, 267.
20
25. 1b: White solid, mp 160–162 ꢀC, ½aꢁD À100.0ꢀ (c 0.16,
1
CHCl3), H NMR (250 MHz, CDCl3) d 1.12 (s, 3H), 1.25 (m,
6H), 1.6 (s, 3H), 1.7 (s, 3H), 1.8 (s, 3H), 2.14–2.50 (m, 7H), 2.2
(s, 3H), 2.4 (s, 3H), 3.76 (d, J=7.4 Hz, 1H), 4.28 (dd, J=21.3,
8.4 Hz, 1H), 4.44 (b, 1H), 4.94 (m, 2H), 5.29–5.36 (m, 3H),
5.64 (d, J=7.4 Hz, 1H), 5.74 (d, J=7.2 Hz, 1H), 6.25–6.28 (m,
3H), 6.45 (d, J=15.9 Hz, 1H), 7.31–7.48 (m, 2H), 7.87 (d,
J=7.5 Hz, 1H), 8.16, (s, 1H). 13C NMR (62.9 MHz, CDCl3) d
5.3, 9.6, 10.0, 14.0, 16.3, 18.2, 18.6, 18.8, 21.3, 22.6, 23.0, 24.8,
25.2, 27.4, 30.8, 32.3, 38.5, 40.8, 45.7, 53.8, 67.4, 67.9, 68.0,
70.8, 76.0, 76.2, 80.0, 116.1, 120.3, 124.5, 124.5, 125.0, 125.1,