AN EFFICIENT METHOD FOR THE OPTICAL RESOLUTION OF 3-HYDROXY-2-SUBSTITUTED-4-ALKYNOATES - A HIGHLY STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-BENGAMIDE-E

被引：28

作者：

MUKAI, C ^{[1
]}

KATAOKA, O ^{[1
]}

HANAOKA, M ^{[1
]}

机构：

[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA,ISHIKAWA 920,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 18期

关键词：

D O I：

10.1021/jo00123a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.

引用

页码：5910 / 5918

页数：9

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