THE SYNTHESIS OF (Z)-PENTA-2,4-DIEN-1-OL AND SUBSTITUTED (E)-PENTADIENOLS BY THE STEREOCHEMICALLY CONTROLLED HORNER-WITTIG REACTION

被引：15

作者：

BROWN, PS ^{[1
]}

GREEVES, N ^{[1
]}

MCELROY, AB ^{[1
]}

WARREN, S ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 06期

关键词：

D O I：

10.1039/p19910001485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylation of Ph2P(O)Me with a lactone gives a Horner-Wittig intermediate with a Z-double bond protected as a Diels-Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol. Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner-Wittig reaction. The geometry of only one double bond can be controlled.

引用

页码：1485 / 1492

页数：8

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