TOTAL SYNTHESIS AND ABSOLUTE STEREOSTRUCTURE OF (+)-DYSIDEAPALAUNIC ACID

被引：26
|
作者：
HAGIWARA, H
UDA, H
机构：
[1] Chemical Research Institute of Non-aqueous Solutions, Tohoku University, Aoba-ku, 980 Sendai, Katahira
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 08期
关键词：
D O I：
10.1039/p19910001803
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of (+)-dysideapalaunic acid, a sesterterpenic aldose reductase inhibitor, has been accomplished. Starting from optically active (8aS)-(+)-3,4,8,8a-tetrahydro-5,8a-dimethylnaphthalene-1,6(2H,7H)-dione, (5S)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5,8a-dimethyl-5-(4-methylpent-3-enyl)naphthalen-1 (2H)-one ethylene acetal has been synthesized in eight steps involving reductive allylation, deoxygenation, and a Wittig condensation. Transformation of this ethylene acetal via methylation at C-2, Grignard addition, and a Horner-Emmons reaction furnished the required (+)-acid in eight steps. Thus, the absolute stereochemistry of the (+)-acid has been established as (4aS,5S,8aS).
引用
收藏
页码：1803 / 1807
页数：5
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