Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones:: An application of novel oxiranyl "remote" anions

被引：30

作者：

Lertvorachon, J ^{[1
]}

Thebtaranonth, Y ^{[1
]}

Thongpanchang, T ^{[1
]}

Thongyoo, P ^{[1
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 13期

关键词：

D O I：

10.1021/jo010259f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereospecific deprotonation of the epoxy proton at the beta -position of the alpha,beta -epoxy esters 5 and 6 yielded oxiranyl "remote" anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones II and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring alpha -methylenebis-gamma -butyrolactones, 1.

引用

页码：4692 / 4694

页数：3

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