Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

被引：46

作者：

Al-Maharik, N ^{[1
]}

Botting, NP ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON | 2003年 / 59卷 / 23期

关键词：

lupiwighteone; Claisen-Cope rearrangement; Mitsunobu reaction;

D O I：

10.1016/S0040-4020(03)00579-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4177 / 4181

页数：5

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