Biomimetic conversion of (3S)-(-)-neodictyoprolenol to optically pure (1S,2R)-(-)-dictyopterene B, marine algal sex pheromone.
نویسندگان
چکیده
Both enantiomers of (3S)-(-)- and (3R)-(+)-Neodictyoprolenol [(3S,5Z,8Z)-(-)-1,5,8-undecatrien-3-ol] were successfully converted to the algal sex pheromone, (1S,2R)-(-)-dictyopterene B and (1R,2S)-(+)-dictyopterene B in high enantiomeric purities (e. e. > 99%), respectively, by the biomimetic reaction involving phosphorylation and elimination under a mild condition.
منابع مشابه
Neodictyoprolenol and dictyoprolenol, the possible biosynthetic intermediates of dictyopterenes, in the Japanese brown algae Dictyopteris.
Neodictyoprolenol [(-)-(3S)-(1,5Z,8Z)-undecatrien-3-ol] and dictyoprolenol [(-)-(3S)-(1,5Z,8Z)-undecadien-3-ol]), which had been proposed as possible biosynthetic intermediates of the sex pheromones of marine brown algae such as dictyopterene B [(-)-trans-1-((1'E,3'Z)-hexadienyl)-2-vinylcyclopropane], D' [(+)-6-((1'Z)-butenyl)-1,4-cycloheptadiene] and C' [(+)-6-butyl-1,4-cycloheptadiene], were ...
متن کاملChemo-Enzymatic Syntheses of Both Enantiomers of Neodictyoprolenol and Neodictyoprolene; Possible Biosynthetic Intermediates of Sex Pheromones in Brown Algae
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi 753-8515, Japan. Fax: +81-839-33-5849. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 54c, 1027-1032 (1999); received June 7/July 12, 1999 Algae, Enantioselective Synthesis, Neodictyoprolene, Pheromones Neodictyoprolenol [(-)-(5')-(l,5Z,8Z)-und...
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ورودعنوان ژورنال:
- Zeitschrift fur Naturforschung. C, Journal of biosciences
دوره 58 1-2 شماره
صفحات -
تاریخ انتشار 2003