Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is r...

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Bibliographic Details
Main Authors: Danny Geerdink, Jeffrey Buter, Teris A. van Beek, Adriaan J. Minnaard
Format: Article
Language:English
Published: Beilstein-Institut 2014-04-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
asymmetric catalysis
copper
deoxypropionates
natural products
sex pheromone
Trichogramma turkestanica
Online Access:https://doi.org/10.3762/bjoc.10.71
Description
Summary:Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner–Wadsworth–Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%.
ISSN:1860-5397

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