SYNTHESIS OF (RS)-ABSCISIC ACID

被引：117

作者：

ROBERTS, DL

HECKMAN, RA

HEGE, BP

BELLIN, SA

机构：

[1] Research Department, R. J. Reynolds Tobacco Company, Winston-Salem, North Carolina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 09期

关键词：

D O I：

10.1021/jo01273a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step synthesis of 3-methyl-5-(1-hydroxy-4-keto-2,6,6-trimethyl-2-cyclohexen-1-yl)-cis,trans-2,4-pentadienoic acid (abscisic acid) has been developed. A novel t-butyl chromate oxidation of ±-ionone gave 4-(1hydroxy- 4-keto-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (3) which was converted into the ethyl ester of abscisic acid by a seldom used variation of the Wittig reaction. Basic hydrolysis of the ester gave approximately equal quantities of abscisic acid and its trans,trans isomer. An alternate route starting with ethyl ±ionylideneacetate is also described. © 1968, American Chemical Society. All rights reserved.

引用

页码：3566 / +

页数：1

共 34 条

[1]

Addicott F. T., 1964, REGULATEURS NATURELS, P687

[2] ABSCISIC ACID - A NEW NAME FOR ABSCISIN 2 (DORMIN) [J].