Biomimetic Conversion of (3S)-(-)-Neodictyoprolenol to Optically Pure (1S,2R)-(-)-Dictyopterene B, Marine Algal Sex Pheromone

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 58, Issue 1-2, 2003, Pages 109-112

  Kajiwara, Tadahiko ^a   Yamamoto, Yuuko ^a   Akakabe, Yoshihiko ^a   Matsui, Kenji ^a   Shimizu, Hiroshi ^a   Kawai, Tesuo ^b  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b Shiono Koryo Kaisha Ltd   (Japan)

Author keywords

Biomimetic Conversion; Marine Algae; Pheromones

Indexed keywords

ALGAE, BROWN; FATTY ALCOHOLS; INDICATORS AND REAGENTS; JAPAN; SEX ATTRACTANTS; STEREOISOMERISM;

ALGAE; EUKARYOTA;

EID: 0345118192     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2003-1-219     Document Type: Article

References (14)

1. Abraham W. D., and Cohen T. (1991), Biogenetically inspired stereospecific synthesis of the dienylvinylcyclo-propane gamete attractant dictyopterene B. J. Am. Chem. Soc. 113, 2313-2314.
2. Boland W., and Müller D. G. (1987), On the odor of the mediterranean seaweed Dictyopteris membranacea; new C11-hydrocarbons from marine brown algae-III. Tetrahedron 28, 307-310.
3. Kajiwara T., Nakatomi T., Sasaki Y., and Hatanaka A. (1980), Stereoselective synthesis of optically active dictyopterenes A and B and their geometrical isomers. Agric. Biol. Chem., 44, 2099-2104.
4. Kajiwara T., Kodama K., Hatanaka A., and Matsui K. (1993), Volatile compounds from Japanese marine brown algae. In Bioactive volatile attractant from plants. Am. Chem. Soc. Symp. Ser. 525, 103-120.
5. Moore R. E., Pettus J. A., Jr., and Mistysyn J. (1974), Odoriferous C11 hydrocarbons from Hawaiian Dictyopteris. J. Org. Chem. 39, 2201-2207.
6. Moore R. E. (1977), Volatile compounds from Marine Algae. Acc. Chem. Res. 10, 40-47.
7. Müller D. G., Jaenicke L., Donike M., and Akintobi T. (1971), Sex attractant in a brown alga: chemical structure. Science, 171, 815-817.
8. Müller D. G., Clayton M. N., Grassman G., Boland W., Marner F.-J., Schotten T., and Jaenicke L. (1985), Cys-tophorene and hormosirene, sperm attractants in Australian brown algae. Naturwissenschaften 72, 97-99.
9. Schneider M. P., and Goldbach M. (1980), Facile synthesis of fucoserratene and the (±)-dictyopterenes B, D, and D' (= ectocarpene): constituents of marine brown algae. J. Am. Chem. Soc. 102, 6114-6116.
10. Schotten T., Boland W., and Jaenicke L. (1985), Synthesis of enantiomerically pure pheromones of south-pacific brown algae: hormosirene and dictyopterene A. Helv. Chim. Acta 68, 1186-1192
11. Suzuki M., Kowata N., and Kurosawa E. (1981), Epicu-benol and related sesquiterpenoids from the brown alga Dictyopteris divaricata. Bull. Chem. Soc. Jpn. 54, 2366-2368.
12. Yamada K., Tan H., Tatematsu H., and Ojika M. (1986), Dictyoprolene and neodictyoprolene, two new odoriferous compounds from the brown alga Dictyopteris prolifera: structures and synthesis. Tetrahedron 42, 3775-3780.
13. Yamamoto Y., Akakabe Y., Matsui K., Shimidzu H., and Kajiwara T. (1999), Chemo-enzymatic syntheses of both enantiomers of neodictyoprolenol and neodictyoprolene; possible biosynthetic intermediates of sex pheromones in brown algae. Z. Naturforsch. 54c, 1027-1032.
14. Yamamoto Y., Akakabe Y., Matsui K., Shimidzu H. and Kajiwara T. (2000), Neodictyoprolenol and dictyopro-lenol, the possible biosynthetic intermediates of dictyopterenes, in the Japanese brown algae Dictyopteris.