Tetrahedron

Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester

T Berkenbusch, R Brückner

文献索引：Berkenbusch, Thilo; Brueckner, Reinhard Tetrahedron, 1998 , vol. 54, # 38 p. 11461 - 11470

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被引用次数: 41

摘要

A method for synthesizing optically active trans, trans-configurated α, β, γ-substituted γ- lactones is presented. Asymmetric hydroxylation of ester 8 with AD mix α (AD mix β) and subsequent dehydration provided butenolide S-6 (R-6). Conjugate addition of Li2 (Me2PhSi) 2Cu (CN) to S-6 followed by alkylation of the resulting enolate led to the stereopure silyllactones 9–11. They furnished the title compounds after oxidative removal ...