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Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae)

✍ Scribed by Diogo M. Vidal; Marcy G. Fonseca; Paulo H.G. Zarbin

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
244 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

The male-produced sex pheromone of Hedypathes betulinus was identified as a mixture of (E)-6,10dimethyl-5,9-undecadien-2-one (geranylacetone) (1) and its respective alcohol (2) and acetate (3). Kinetic resolution of alcohol (2) promoted by CAL-B in organic media provided both, (R)-(À)-(E)-6,10dimethyl-5,9-undecadien-2-yl acetate (3) and (S)-(+)-(E)-6,10-dimethyl-5,9-undecadien-2-ol (2) in high enantiomeric purity. Comparative GC analysis using a chiral column revealed the natural constituents as being (R)-( ) and a mixture of (R)-and (S)-( ) in a ratio of 82.3% and 17.6%, respectively.

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