STUDIES TOWARDS THE SYNTHESIS OF OBTUSENYNE - A CLAISEN REARRANGEMENT APPROACH TO UNSATURATED 9-MEMBERED LACTONES

被引：34

作者：

CURTIS, NR ^{[1
]}

HOLMES, AB ^{[1
]}

LOONEY, MG ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 34期

关键词：

MEDIUM RING; UNSATURATED LACTONE; CLAISEN REARRANGEMENT; VINYL KETENE ACETAL; SELENOXIDE ELIMINATION;

D O I：

10.1016/S0040-4020(01)96169-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An advanced intermediate for the synthesis of the Laurencia oxonane natural product obtusenyne 1, namely the unsaturated nine-membered lactone 3, was efficiently prepared in seven steps from (E)-3-hexenoic acid 7. The key transformation was the Claisen rearrangement of the vinyl ketene acetal 4, which represents novel methodology for the preparation of such unsaturated nine-membered lactones.

引用

页码：7171 / 7178

页数：8

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