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

ABSTRACT: 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%.

SUBMITTER: Geerdink D

PROVIDER: S-EPMC3999798 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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

Geerdink Danny D Buter Jeffrey J van Beek Teris A TA Minnaard Adriaan J AJ

Beilstein journal of organic chemistry 20140402

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, ...[more]

PMID: 24778730

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