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Synthesis of Enantiomerically Pure Pheromones of South-Pacific Brown Algae: Hormosirene and Dictyopterene A

✍ Scribed by Theo Schotten; Wilhelm Boland; Lothar Jaenicke

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
442 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Hormosirene ((−)‐1; (1__R__,2__R__)‐1‐((1__E__,3__Z__)‐1,3‐hexadienyl)‐2‐vinylcyclopropane) is the specific sex attractant of several brown algae of the Australian shelf, while dictyopterene A ((+)‐2; (1__R__, 2__R__)‐1‐((1__E__)‐1‐hexenyl)‐2‐vinylcyclopropane) is found as a minor constituent of the pheromone bouquets. The asymmetric synthesis of the two hydrocarbons is performed by resolution of the amides (−)‐5 and (+)‐5a obtained from (−)‐(R)‐2‐phenylglycinol and racemic trans‐vinylcyclopropanecarboxylic acid (rac‐4) on silica gel. Both diastereoisomers are obtained optically pure. They are converted by stereoselective Wittig olefination into the title compounds. Compound (−)‐1 is the active mating pheromone of the reproductive system of the seaweed Xiphophora chondrophylla as established by biological‐activity assays.

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