HIGHLY STEREOSELECTIVE SYNTHESIS OF (+/-)-ALPHA-MULTISTRIATIN

被引：56

作者：

BARTLETT, PA

MYERSON, J

机构：

[1] Department of Chemistry, University of California, Berkeley

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 10期

关键词：

D O I：

10.1021/jo01324a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Erythro-2,4-Dimethyl-5-hexenoic acid, available from meso-2,4-dimethylglutaric anhydride, is functionalized in a highly stereoselective manner by iodolactonization. Subsequent methanolysis of the iodo lactone and conversion of the ester to the ethyl ketone provide the desired cyclization substrate 2. Lewis acid catalyzed cyclization of 2 then affords (.+-.)-.alpha.-multistriatin of more than 95% purity in a sequence which necessitates no column or vapor phase chromatography purification steps. [Multistriatin is one component of the aggregation pheromone of Scolytus multistriatus].

引用

页码：1625 / 1627

页数：3

共 12 条

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