Synthesis of (+)-ginnol, a type Rlong-CH(OH)-R′long alcohol, by an asymmetric β,γ-unsaturated ester→γ-butyrolactone conversion

被引：24

作者：

Berkenbusch, T ^{[1
]}

Bruckner, R ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 38期

关键词：

alcohols; asymmetric synthesis; lactones; osmylation;

D O I：

10.1016/S0040-4020(98)00688-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of (+)-ginnol (17) illustrates how Sharpless' asymmetric dihydroxylation may be used for the asymmetric synthesis of monoalcohols. The dihydroxylation was perfomed with AD mix alpha and the unsaturated ester trans-9. The resulting lactone cis-13 was dehydrated giving butenolide 13 (96.2% ee) from where we proceeded to the title compound 17 in three steps. Butenolide 13 showed 88-94%ee when ester trans-9 contained cis-isomer due to too forcing reaction condition on the way to the precursor acids trans- and cis-7. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：11471 / 11480

页数：10

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