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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Published inBeilstein journal of organic chemistry Vol. 10; no. 1; pp. 761 - 766
Main Authors Geerdink, Danny, Buter, Jeffrey, van Beek, Teris A, Minnaard, Adriaan J
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 02.04.2014
Subjects
absolute-configuration
asymmetric catalysis
Chemistry
convergent
copper
deoxypropionates
elucidation
Full Research Paper
mycobacterium-tuberculosis
natural products
phthioceranic acid
reductions
sex pheromone
Trichogramma turkestanica
natural products
copper
deoxypropionates
asymmetric catalysis
Trichogramma turkestanica
sex pheromone
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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%.
Bibliography:ObjectType-Article-1
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.10.71