Absolute configuration of marine diterpenoid kalihinol A

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 8015-8017

  Shimomura, Masako ^a   Miyaoka, Hiroaki ^a   Yamada, Yasuji ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Antimalarial compounds; Marine metabolites; Natural products; Terpenes; Terpenoids

Indexed keywords

BENZAMIDE DERIVATIVE; DITERPENOID; KALIHINOL A; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; STRUCTURE ANALYSIS;

EID: 0033527603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01664-0     Document Type: Article

References (20)

1. Chang, C. W. J.; Patra, A.; Roll, D. M.; Scheuer, P. J.; Matsumoto, G. K.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 4644-4646.
2. Patra, A.; Chang, C. W. J.; Scheuer, P. J.; Van Duyne, G. D.; Matsumoto, G. K.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 7981-7983.
3. Chang, C. W. J.; Patra, A.; Baker, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1987, 109, 6119-6123.
4. Omar, S.; Albert, C.; Fanni, T.; Crews, P. J. Org. Chem. 1988, 53, 5971-5972.
5. Fusetani, N.; Yasumuro, K.; Kawai, T.; Natori, T.; Brinen, L.; Clardy, J. Tetrahedron Lett. 1990, 31, 3599-3602.
6. Alvi, K. A.; Tenenbaum, L.; Crews, P. J. Nat. Prod. 1991, 54, 71-78.
7. Trimurtulu, G.; Faulkner, D. J. J. Nat. Prod. 1994, 57, 501-506.
8. Braekman, J. C.; Daloze, D.; Gregoire, F.; Popov, S.; Van Soest, R. Bull. Soc. Chim. Belg. 1994, 103, 187-191.
9. Rodríguez, J.; Nieto, R. M.; Hunter, L. M.; Diaz, M. C.; Crews, P.; Lobkovsky, E.; Clardy, J. Tetrahedron 1994, 50, 11079-11090.
10. Okino, T.; Yoshimura, E.; Hirota, H.; Fusetani, N. Tetrahedron Lett. 1995, 36, 8637-8640.
11. Hirota, H.; Tomono, Y.; Fusetani, N. Tetrahedron 1996, 52, 2359-2368.
12. Fusetani, N. J. Nat. Toxins 1996, 5, 249-259.
13. Okino, T.; Yoshimura, E.; Hirota, H.; Fusetani, N. J. Nat. Prod. 1996, 59, 1081-1083.
14. Wolf, D.; Schmitz, F. J. J. Nat. Prod. 1998, 61, 1524-1527.
15. Miyaoka, H.; Shimomura, M.; Kimura, H.; Yamada, Y.; Kim, H.-S.; Wataya, Y. Tetrahedron 1998, 54, 13467-13474.
16. (a) Kawai, M.; Nagai, U.; Katsumi, M. Tetrahedron Lett. 1975, 3165-3166;
17. (b) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: California, and Oxford University Press: Oxford, 1983; pp. 160-164.
18. Chiral World, http://chiral.icrs.tohoku.ac.jp/CHIRAL/index-e.htm
19. 3) δ 0.98 (3H, s), 1.19 (1H, m), 1.2-1.7 (10H, m), 1.24 (3H, s), 1.29 (3H, s), 1.29 (3H, s), 1.36 (3H, s), 1.90 (1H, dt, J=3.0, 11.3 Hz), 1.95-2.15 (3H, m), 3.22 (1H, d, J=1.5 Hz), 3.72 (1H, dd, J=12.3, 4.4 Hz).
20. 2), 47.0 (CH), 57.4 (C), 57.5 (CH), 65.4 (CH), 73.5 (C), 76.2 (C), 77.0 (C), 125.9 (C), 126.0 (C), 128.3 (CH), 128.6 (CH), 131.9 (CH), 131.9 (CH), 134.4 (C), 134.8 (C), 165.7 (C), 166.1 (C).