ENANTIOMERIC 3,7-DIMETHYLOCTA-1,7-DIENES AS USEFUL CHIRAL BUILDING-BLOCKS - A NEW ACCESS TO BOTH OPTICAL-ANTIPODES OF NATURAL (E)-3,7-DIMETHYLOCT-2-ENE-1,8-DIOL AND (E)-3,7-DIMETHYLOCT-2-ENE-1,8-DICARBOXYLIC ACID

被引：13

作者：

GIERSCH, W ^{[1
]}

SCHULTEELTE, KH ^{[1
]}

机构：

[1] FIRMENICH CO,RECH LABS,CH-1211 GENEVA 8,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 03期

关键词：

D O I：

10.1002/hlca.19900730322

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ozonolysis of the easily available monoterpenoids (−)‐1 and (+)‐1 leads in high yield to the ketoaldehydes (−)‐4 and (+)‐4, which serve as convenient intermediates for efficient new routes to both optical antipodes of the naturally occurring octenediol (E)‐2 (Monarch butterfly secretion product) and octene‐dicarboxylic acid (E)‐3 (Callosobruchus chinensis sex pheromone). All steps proceed with almost complete retention of configuration, ensuring the synthesis of the target compounds with high optical purity. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：733 / 739

页数：7

共 22 条

[1] RECENT ADVANCES IN ASYMMETRIC-SYNTHESIS .2. [J].