New mycalolides from the marine sponge Mycale magellanica and their interconversion

Journal of Natural Products

Volumn 61, Issue 9, 1998, Pages 1164-1167

  Matsunaga, Shigeki ^a   Sugawara, Takeo ^a   Fusetani, Nobuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

30 HYDROXYMYCALOLIDE A; 32 HYDROXYMYCALOLIDE A; 38 HYDROXYMYCALOLIDE B; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG CONFORMATION; DRUG ISOLATION; LEUKEMIA L 1210; MOUSE; NONHUMAN; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; LEUKEMIA L1210; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; PORIFERA; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEREOISOMERISM;

ANIMALIA; INVERTEBRATA; MYCALE; MYCALE MAGELLANICA; PORIFERA;

EID: 0031661330     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np980102r     Document Type: Article

References (15)

1. Bioactive Marine Metabolites. 84. Part 83: Matsunaga, S.; Kamimura, T.; Fusetani, N. J. Nat. Prod. 1998, 61, 671-672.
2. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett. 1985, 26, 3483-3486.
3. Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Thompson, A. M. J. Org. Chem. 1990, 50, 223-227.
4. Fusetani, N.; Sugawara, T.; Matsunaga, S.; Hirota, H. J. Org. Chem. 1991, 56, 4971-4974.
5. Northcote, P. T.; Blunt, J. W.; Munro, M. H. G. Tetrahedron Lett. 1991, 32, 6411-6414.
6. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett. 1989, 30, 2809-2812. Subsequently, two related macrolides and mycalolide C were isolated from the stony coral Tubastrea faulkneri (Rashid, M. A.; Gustafson, K. R.; Cardellina, J. H., II; Boyd, M. R. J. Nat. Prod. 1995, 58, 1120-1125).
7. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett. 1989, 30, 2809-2812. Subsequently, two related macrolides and mycalolide C were isolated from the stony coral Tubastrea faulkneri (Rashid, M. A.; Gustafson, K. R.; Cardellina, J. H., II; Boyd, M. R. J. Nat. Prod. 1995, 58, 1120-1125).
8. Saito, S.; Watabe, S.; Ozaki, H.; Fusetani, N.; Karaki, H. J. Biol. Chem. 1994, 269, 29710-29714.
9. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360-1363.
10. 1H NMR data (data not shown).
11. + in the FABMS] is most likely the C-30-epimer of 7.
12. It was necessary to reduce the C-7 ketone to accomplish a clean conversion.
13. Production of compound 10 is rationalized as intramolecular Michael-type addition of the C-24 alcohol to the C-19-C-20 unsaturated olefin. In compound 10, the olefinic signals for H-19 and H-20 were replaced by low-field methylenes at δ 3.04 (H-19a), 3.22 (H-19b), and an oxygenated methine at 4.25 (H-20).
14. Without chiroptical data interconversion among 1-6 only reveals the identity of relative stereochemistry.
15. For experimental details, see ref 4.