Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica
نویسندگان
چکیده
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%.
منابع مشابه
Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae)
Females of the parasitoid wasp Trichogramma turkestanica produce the putative polydeoxypropionates (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4-diene and (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4-dien-1-ol or their enantiomers as sex specific volatiles. The structures were assigned on the basis of GC-MS investigations using synthetic reference compounds.
متن کاملEvaluating the Efficiency of Trichogramma Pintoii and Bacillus Thuringiensis Var. Kurstaki on Corn Stem Borer, Ostrinia Nubilalis (Lepidoptera:Pyralidae), in Corn Fields of Moghan Plain
In order to evaluate the efficiency of biocontrol agents of corn stem borer ,Ostrinia nubilalis, experiment was conducted in a randomized complete block by five treatments and four replication, including, Indoxacarb (Avant)®, Trichogrammawasps, Bacillus thuringiensis var: kurstaki, integration of Trichogramma sp. and Bt., and cont...
متن کاملEvaluating the Efficiency of Trichogramma Pintoii and Bacillus Thuringiensis Var. Kurstaki on Corn Stem Borer, Ostrinia Nubilalis (Lepidoptera:Pyralidae), in Corn Fields of Moghan Plain
In order to evaluate the efficiency of biocontrol agents of corn stem borer ,Ostrinia nubilalis, experiment was conducted in a randomized complete block by five treatments and four replication, including, Indoxacarb (Avant)®, Trichogrammawasps, Bacillus thuringiensis var: kurstaki, integration of Trichogramma sp. and Bt., and cont...
متن کاملThe origin of a selfish B chromosome triggering paternal sex ratio in the parasitoid wasp Trichogramma kaykai.
This study uses molecular and cytogenetic methods to determine the origin of a B chromosome in some males of the wasp Trichogramma kaykai. This so-called paternal sex ratio (PSR) chromosome transmits only through sperm and shortly after fertilization triggers degeneration of the paternal genome, while keeping itself intact. The resulting embryos develop into haploid B-chromosome-carrying males....
متن کاملHitch-hiking parasitic wasp learns to exploit butterfly antiaphrodisiac.
Many insects possess a sexual communication system that is vulnerable to chemical espionage by parasitic wasps. We recently discovered that a hitch-hiking (H) egg parasitoid exploits the antiaphrodisiac pheromone benzyl cyanide (BC) of the Large Cabbage White butterfly Pieris brassicae. This pheromone is passed from male butterflies to females during mating to render them less attractive to con...
متن کامل