Amphidinolide V, novel 14-membered macrolide from marine dinoflagellate Amphidinium sp.

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 713-716

  Kubota, Takaaki ^a   Tsuda, Masashi ^a   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Cytotoxic; Macrolide; Marine dinoflagellate; Polyene

Indexed keywords

AMPHIDINOLIDE V; CARBENE; EPOXIDE; MACROLIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DINOFLAGELLATE; DRUG STRUCTURE; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY; TUMOR CELL;

EID: 0034728137     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02170-X     Document Type: Article

References (17)

1. (a) Ishibashi, M.; Takahashi, M.; Kobayashi, J. Tetrahedron 1997, 53, 7827-7832.
2. (b) Ishibashi, M.; Kobayashi, J. Heterocycles 1997, 44, 543-572 and references cited therein.
3. Bauer, I.; Maranda, L.; Young, K. A.; Shimizu, Y.; Haung, S. Tetrahedron Lett. 1995, 36, 991-994 and references cited therein.
4. (a) Paul, G. K.; Matsumori, N.; Konoki, K.; Murata, M.; Tachibana, K. J. Mar. Biotechnol. 1997, 5, 124-128 and references cited therein.
5. (b) Doi, Y.; Ishibashi, M.; Nakamichi, H.; Kosaka, T.; Ishikawa, T.; Kobayashi, J. J. Org. Chem. 1997, 62, 3820-3823.
6. Kobayashi, J.; Kubota, T.; Takahashi, M.; Ishibashi, M.; Tsuda, M.; Naoki, H. J. Org. Chem. 1999, 64, 1478-1482.
7. Kobayashi, J.; Takahashi, M.; Ishibashi, M. J. Chem. Soc., Chem. Commun. 1995, 1639-1640.
8. Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Yamasu, T.; Sasaki, T.; Hirata, Y. Tetrahedron Lett. 1986, 27, 5755-5758.
9. Kobayashi, J.; Ishibashi, M.; Wälchli, M. R.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Ohizumi, Y. J. Am. Chem. Soc. 1988, 110, 490-494.
10. Kobayashi, J.; Ishibashi, M.; Murayama, M.; Takamatsu, M.; Iwamura, Y.; Ohizumi, Y.; Sasaki, T. J. Org. Chem. 1990, 55, 3421-3423.
11. Kobayashi, J.; Sato, M.; Ishibashi, M. J. Org. Chem. 1993, 58, 2645-2646.
12. +, 419.2199].
13. Positive mode ESIMS spectra were measured on a Jeol JMS-700TZ spectrometer at -80 V as a focus voltage using a sample dissolved in MeOH with flow rate of 200 μL/min.
14. J values for cis- (4 Hz) and trans-epoxides (1.5 Hz): In Handbook of Proton NMR Spectra and Data; Asahi Research Center, Ed.; Academic Press: Tokyo, 1985; Vol. 1, p. 86.
15. a and b denote low-field and high-field resonances, respectively, of a geminal pair.
16. Relative configurations at C-8, C-9, C-10, and C-13 were R*, S*, S*, and R*, respectively.
17. Molecular mechanics calculations for the four possible diastereomers with respect to C-8, C-9/C-10, and C-13 of 1 were carried out using MacroModel program ver. 6.0 (MM2* force-field). The most stable conformation (total energy; 35.70 kcal/mol) having 8R, 9S, 10S, and 13R-configurations fitted well the conformation shown in Fig. 2, while those of three other possible diastereomers could not be explained from the NOE data of 1. For example, in the most stable conformation of the diastereomer having 8R, 9R, 10R, and 13R-configurations shown below, observation of NOE's for H-6a/H-9 and H-13/H-24b seems to be difficult.