Asymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2, 3-disubstituted epoxide

SF Mayer, H Mang, A Steinreiber…

Index: Mayer, Sandra F.; Mang, Harald; Steinreiber, Andreas; Saf, Robert; Faber, Kurt Canadian Journal of Chemistry, 2002 , vol. 80, # 4 p. 362 - 369

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Citation Number: 14

Abstract

A short total asymmetric synthesis of (+)-exo-and ()-endo-brevicomin ((+)-exo-3 and ()-endo- 3), which are components of the attracting pheromone system of several bark-beetle species belonging to the genera Dendroctonus and Dryocoetes, was accomplished via a chemoenzymatic protocol. The key step consisted of biocatalytic hydrolysis by bacterial epoxide hydrolases of cis-configured 2, 3-disubstituted oxiranes bearing olefinic side ...