Chemoenzymatic synthesis of (+)-docosa-4,15-dien-l-yn-3-ol, a component of the marine sponge Cribrochalina vasculum, and confirmation of the structure, and absolute configuration of the acetylenic alcohol, by lipase-catalysed biotransformations

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1999, Pages 513-518

  Morishita, Kiyoshi ^a   Kamezawa, Makoto ^a   Ohtani, Takehiko ^a   Tachibana, Hojun ^b   Kawase, Mayumi ^b   Kishimoto, Midori ^b   Naoshima, Yoshinobu ^b  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b Konan Chemical Industry Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000751614     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807681b     Document Type: Article

References (11)

1. T. Ohtani, K. Kikuchi, M. Kamezawa, H. Hamatani, H. Tachibana, T. Totani, and Y. Naoshima, J. Client. Soc., Parkin Trans. I, 1996, 961.
2. S. P, Gunasekera, and G. T. Faircloth, J. Org. Chem., 1990,55, 6223.
3. A. Aiello, E. Fattorusso, M. Menna, and M. Pansini, J. Nat. Prod., 1992,55,1275.
4. Y. F. Hallock, J. H. Cradellina II, M. S. Balaschak, M. R. Alexander, T. R. Prather, R. H. Shoemaker, and M. R. Boyd, J. Nat. Prod, 1995,58, 1801.
5. Y. Guo, M. Gavagnin, E. Trivellone, and G. Cimino, Tetrahedron, 1994,50, 13261.
6. M. Kamezawa, M. Kitamura, H. Nagaoka, H. Tachibana, T. Ohtani, and Y. .Naoshima, Liebigs Ann. Chem., 1996, 167; M. Kamezawa, T. Raku, H. Tachibana, T. Ohtani, and Y. Naoshima, Biosci. Biotcchnol. Biochem., 1995, 59, 549; M. Kamezawa, T. Ohtani, T. Raku, H. Tachibana, and Y. Naoshima, Récent Research Developments in Agricultural & Biological Chemistry, vol. 2, Research Signpost, Trivandrum, 1998, p. 63; T. Ohtani, H. Nakatsukasa, M. Kamezawa, H. Tachibana, and Y. Naoshima, J. Mol Cala!. B: Enzym., 1998,4, 53.
7. M. Kamezawa, T. Raku, H. Tachibana, T. Ohtani, and Y. Naoshima, Biosci. Biotcchnol. Biochem., 1994,58, 598.
8. E. Breitmeier, and W. Voelter, Carbon-13 NAfR Spectroscopy: HighResolution Methods, and Applications in Organic Chemistry, and Biochemistry, 3rd edn., VCH, New York, 1987, p. 192; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, 1972, p. 80.
9. Y. Naoshima, H. Hasegawa, T. Nishiyama, and A. Nakamura, Bull Chem. Soc. Jpn., 1989,62,608.
10. J. G. Millar, A. C. Oehlschlager, and J. W. Wong, J. Org. Chem., 1983, 48, 4404; C. A. Brown, and V. K. Ahuji, J. Chem. Soc., Chem. Commun., 1973,553.
11. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C. J. Sih, J. Am. Chem. Soc., 1982,104,7294.