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Synthesis of Enantiomerically Pure Pheromones of South‐Pacific Brown Algae: Hormosirene and Dictyopterene A
Author(s) -
Schotten Theo,
Boland Wilhelm,
Jaenicke Lothar
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680514
Subject(s) - chemistry , diastereomer , sex pheromone , brown algae , algae , wittig reaction , stereochemistry , pheromone , stereoselectivity , optically active , botany , organic chemistry , catalysis , biology
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.