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
收藏
页码：4177 / 4181
页数：5
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