Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

被引：23

作者：

Beszant, S ^{[1
]}

Giannini, E ^{[1
]}

Zanoni, G ^{[1
]}

Vidari, G ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(02)00335-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1245 / 1255

页数：11

共 33 条

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