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Pheromone Synthesis, CXIII. Synthesis of the Enantiomers of (3Z,6Z)-cis-9,10-Epoxy-1,3,6-henicosatriene and (3Z,6Z)-cis-9,10-Epoxy-1,3,6-icosatriene, the New Pheromone Components ofHyphantria cunea

✍ Scribed by Mori, Kenji ;Takeuchi, Tadashi

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 554 KB
Volume: 1989
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198919890180

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✦ Synopsis

Epoxidation, asymmetric / Epoxytriene pheromones / Lithium dialkylcuprates / Pheromones, enantiomerically pure Fall webworm moth (Hyphantria cunea) is a notorious pest known as Amerika-shirohitori in Japan or the American white moth in the U.S.S.R. Three pheromone components of the female moth were known: (32,62)-cis-9,10-ep-oxy-3,6-henicosadiene (A), (92.3 22)-9,12-octadecadienal (B) and (9~,122,152)-9,12,15-octadecatrienal (C)233). Our synthesis of the enantiomers of A established the absolute configuration of natural A as (9S,10R)4,5). A blend of (9S,10R)-Scheme 1. Pheromone components of Hyphantria cunea and the synthetic plan for the epoxide 1

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