Colopsinol A, a novel polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp.

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1478-1482

  Kobayashi, Jun'ichi ^a   Kubota, Takaaki ^a   Takahashi, Miho ^a   Ishibashi, Masami ^a   Tsuda, Masashi ^a   Naoki, Hideo ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; NATURAL PRODUCT; POLYKETIDE;

ARTICLE; DINOFLAGELLATE; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 0033525493     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981882b     Document Type: Article

References (20)

1. Ishibashi, M.; Kobayashi, J.Heterocycles 1997, 44, 543-572 and references therein.
2. (a) Satake, M.; Murata, M.; Yasumoto, T.; Fujita, T.; Naoki, H. J. Am. Chem. Soc. 1991, 113, 9851-9861.
3. (b) Paul, G. K.; Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1995, 36, 6279-6282.
4. Paul, G. K.; Matsumori, N.; Konoki, K.; Murata, M.; Tachibana, K. J. Mar. Biotechnol. 1997, 5, 124-128.
5. Doi, Y.; Ishibashi, M.; Nakamichi, H.; Kosaka, T.; Ishikawa, T.; Kobayashi, J. J. Org. Chem. 1997, 62, 3820-3823.
6. Ishibashi, M.; Takahashi, M.; Kobayashi, J. Tetrahedron 1997, 53, 7827-7832.
7. Davis, D. G. J. Magn. Reson. 1991, 91, 665.
8. Fukushi, E.; Tanabe, S.; Watanabe, M.; Kawabata, J. Magn. Reson. Chem. 1998, 36, 741-746.
9. Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Hirata, Y. J. Chem. Soc., Perkin Trans. 1 1989, 101-103.
10. Kalinnowski, H.-O.; Berger, S.; Braun, S. In Carbon-13 NMR Spectroscopy; John Wiley & Sons: Chichester, 1988; pp 442, 499, and 509.
11. C 82.1): Kobayashi, J.; Kondo, K; Ishibashi, M.; Wälchli, M. R.; Nakamura, T. J. Am. Chem. Soc. 1993, 115, 6661-6665.
12. NOE experiments are as follows: irradiation of H-4 yielded NOEs at H-2 (3.4%), H-3 (2.9%), and H-5 (5.0%); irradiation of H-5 yielded NOEs at H-4 (5.9%), and H-6 (4.4%); irradiation of H-8 yielded NOEs at H-2 (1.5%), H-6β (1.5%), and H-7β (5.1%).
13. 3
14. Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Yamasu, T.; Sasaki, T.; Hirata, Y. Tetrahedron Lett. 1986, 27, 5755-5758.
15. c 32.8) on the Z-double bond of patellazole B (Corley, D. G.; Moore, R. E.; Paul, V. J. J. Am. Chem. Soc. 1988, 110, 7920-7922).
16. c 32.8) on the Z-double bond of patellazole B (Corley, D. G.; Moore, R. E.; Paul, V. J. J. Am. Chem. Soc. 1988, 110, 7920-7922).
17. 13
18. Kobayashi, J.; Doi, Y.; Ishibashi, M. J. Org. Chem. 1994, 59, 255-257
19. Naoki, H. LC/MS no Jissai; Harada, K., Oka, H., Eds.; Kodansha: Tokyo, 1996; pp 225-252.
20. Shimbulan, C. M. G.; Taki, T.; Tamiya-Koizumi, K.; Suzuki, M.; Savosky, E.; Shoji, M.; Yoshida, S. Biochim. Biophys. Acta 1994, 1205, 68-74.