Absolute stereochemistry of penaresidins A and B

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6775-6776

  Kobayashi, Jun'ichi ^a   Tsuda, Masashi ^a   Cheng, Jie Fei ^a   Ishibashi, Masami ^a   Takikawa, Hirosato ^b   Mori, Kenji ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PENARESIDIN A; PENARESIDIN B; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

EID: 0030576922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01465-7     Document Type: Article

References (11)

1. 1. Kobayashi, J.; Ishibashi, M. Heterocycles, 1996, 42, 943-970.
2. 2. Kobayashi, J.; Cheng, J.-F.; Ishibashi, M.; Wälchli, M. R.; Yamamura, S.; Ohizumi, Y. J. Chem. Soc. Perkin Trans 1, 1991, 1135-1137.
3. 3. a) Takikawa, H.; Maeda, T.; Mori, K. in Symposium Papers of 37th Symposium on the Chemistry of Natural Products, Tokushima, Japan, 1995, pp. 49-54.
4. b) Takikawa, H.; Maeda, T.; Mori, K. Tetrahedron Lett., 1995, 36, 7689-7692.
5. c) Takikawa, H.; Maeda, T.; Seki, M.; Koshino, H.; Mori, K. J. Chem. Soc., Perkin Trans. 1, in press.
6. 2-5), 1.77 (3H, s, N-Ac), 3.49 (3H, s, OMe), 3.53 (3H, s, OMe), 3.54 (3H, s, OMe), 4.18 (1H, m, H-4), 4.32 (1H, br.s, H-2), 4.67 (1H, dd, J, = 1.1 and 11.8 Hz, H-1), 5.07 (1H, dd, J, = 3.9 and 7.1 Hz, H-3), 5.07 (1H, m, H-15), 5.15 (1H, dd, J, = 2.5 and 11.8 Hz, H-1), and 7.35 - 7.55 (15H, m, Ph)
7. 2-13), 1.53 (1H, m, H-14), 1.58 (1H, m, H-16), 1.60 (1H, m, H-17), 1.61 (1H, m, H-5), 1.77 (1H, m, H-5), 1.77 (3H, s, N-Ac), 3.49 (3H, s, OMe), 3.54 (3H, s, OMe), 3.55 (3H, s, OMe), 4.18 (1H, m, H-4), 4.32 (1H, br.s, H-2), 4.67 (1H, dd, J, = 1.1 and 11.8 Hz, H-1), 5.07 (1H, dd, J = 3.9 and 7.1 Hz, H-3), 5.17 (1H, m, H-15), 5.15 (1H, dd, J = 2.5 and 11.8 Hz, H-1), and 7.35 - 7.55 (15H, m, Ph)
8. 2-5), 3.49 (3H, s, OMe), 3.53 (3H, s, OMe), 3.54 (3H, s, OMe), 4.19 (1H, m, H-4), 4.39 (1H, br.s, H-2), 4.49 (1H, dd, J = 1.1 and 11.8 Hz, H-1), 5.23 (1H, dd, J = 3.9 and 7.1 Hz, H-3), 5.09 (1H, m, H-15), 5.28 (1H, dd, J = 2.5 and 11.8 Hz, H-1), and 7.35 - 7.55 (15H, m, Ph)
9. 2-13), 1.39 (1H, m, H-16), 1.45 (1H, m, H-17), 1.52 (1H, m, H-16), 1.53 (1H, m, H-5), 1.59 (1H, m, H-14), 1.61 (1H, m, H-5), 1.74 (3H, s, N-Ac), 3.53 (3H, s, OMe), 3.54 (3H, s, OMe), 3.55 (3H, s, OMe), 4.19 (1H, m, H-4), 4.39 (1H, br.s, H-2), 4.49 (1H, dd, J = 1.1 and 11.8 Hz, H-1), 5.23 (1H, dd, J = 3.9 and 7.1 Hz, H-3), 5.17 (1H, m, H-15), 5.28 (1H, dd, J = 2.5 and 11.8Hz, H-1), and 7.35 ~ 7.55 (15H, m, Ph)
10. 1H NMR spectrum of each MTPA ester (5 ~ 8) suggested that there were no rotational isomers around the amide bond of the N-acetyl group.
11. 9. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4095.