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Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals.

ABSTRACT: 2,3-Butanediacetal derivatives were used for the stereoselective synthesis of unsymmetrically substituted cis-epoxides. The procedure was applied for the preparation of both enantiomers of disparlure and monachalure, the components of the sex pheromones of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha) using methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting material.

SUBMITTER: Drop A

PROVIDER: S-EPMC7136567 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals.

Drop Adam A Wojtasek Hubert H Frąckowiak-Wojtasek Bożena B

Beilstein journal of organic chemistry 20200403

2,3-Butanediacetal derivatives were used for the stereoselective synthesis of unsymmetrically substituted cis-epoxides. The procedure was applied for the preparation of both enantiomers of disparlure and monachalure, the components of the sex pheromones of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha) using methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting mat ...[more]

PMID: 32280390

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