Absolute stereochemistry of keramaphidin B

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8203-8204

  Kobayashi, Jun'ichi ^a   Kawasaki, Naoko ^a   Tsuda, Masashi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; DRUG STRUCTURE; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE;

EID: 0030569407     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01861-8     Document Type: Article

References (12)

1. 1. Kobayashi, J.; Tsuda, M.; Kawasaki, N.; Matsumoto, K.; Adachi, T. Tetrahedron Lett., 1994, 35, 4383-4386.
2. 2. (a) Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. J. Am. Chem. Soc., 1986, 108, 6404-6405.
3. (b) Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y.; Tomotake, Y.; Matsuzaki, T.; Hirata, Y. Tetrahedron Lett., 1987, 28, 621-624.
4. 3. Sakai, R.; Kohmoto, T.; Higa, T.; Jefford, C. W.; Bernardinelli, G, Tetrahedron Lett., 1987, 28, 5493-5496.
5. 4. Baldwin, J. E.; Whitehead, R. C. Tetrahedron Lett., 1992, 33, 2059-2062.
6. 5. Tsuda, M.; Inaba, K.; Kawasaki, N.; Honma, K.; Kobayashi, J. Tetrahedron, 1996, 52, 2319-2324.
7. 3: δ 0.95 (1H, dd, J = 6.3 and 10.4 Hz, H-4a), 1.04 (1H, m, H-5), 1.35 (1H, m, H-17), 1.37 (1H, m, H-12), 1.38 (1H, m, H-20), 1.42 (1H, m, H-5), 1.43 (1H, m, H-12), 1.44 (1H, m, H-17), 1.48 (1H, m, H-25), 1.54 (1H, m, H-20), 1.59 (1H. m, H-18), 1.67 (1H, m, H-25), 1.72 (1H, m, H-3), 1.91 (1H, m, H-26), 1.92 (1H, m, H-4), 1.94 (1H, m, H-18), 1.97 (1H, m, H-8), 2.18 (1H, m, H-19), 2.24 (1H, d, J = 16.7 Hz, H-8), 2.24 (1H, m, H-11), 2.25 (1H, m, H-26), 2.34 (1H, m, H-3), 2.54 (1H, m, H-6), 2.82 (1H, m, H-6), 3.08 (1H, s, H-1), 3.11 (1H, m, H-19), 3.18 (1H, m, H-11), 3.50 (3H, s, OMe), 4.32 (1H, d, J = 4.8 Hz, H-10), and 7.35 ∼ 7.55 (5H, m, Ph).
8. 3: δ 0.79 (1H, dd, J = 5.8 and 9.8 Hz, H-4a), 0.96 (1H, m, H-5), 1.35 (1H, m, H-12), 1.36 (1H, m, H-5), 1.38 (1H, m, H-17), 1.39 (1H, m, H-12), 1.39 (1H, m, H-20), 1.45 (1H, m, H-17), 1.53 (1H, m, H-25), 1.55 (1H, m, H-18), 1.55 (1H, m, H-20), 1.59 (1H, m, H-3), 1.69 (1H, m, H-4), 1.75 (1H, m, H-25), 1.91 (1H, m, H-18), 2.03 (1H, m, H-8), 2.06 (1H, m, H-26), 2.16 (1H, m, H-3), 2.19 (1H, m, H-19), 2.28 (1H, d, J= 13.5 Hz, H-8), 2.30 (1H, m, H-11), 2.43 (1H, m, H-26), 2.50 (1H, m, H-6), 2.77 (1H, m, H-6), 3.10 (1H, m, H-19), 3.19 (1H, s, H-1), 3.26 (1H, m, H-11), 3.53 (3H, m, s, OMe), 4.30 (1H, d, J = 5.2 Hz, H-10), and 7.35 ∼ 7.55 (5H, m, Ph).
9. 8. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4095.
10. 9. Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem., 1992, 57, 2480-2483.
11. 10. Tsuda, M.; Kawasaki, N.; Kobayashi, J. Tetrahedron, 1994, 50, 7957-7960.
12. 11. Kong, F.; Andersen, R. J. Tetrahedron , 1995, 51, 2895-2906.