SYNTHETIC STUDIES ON THE OPHIOBOLANE SESTERTERPENES - CONSTRUCTION OF AN OPTICALLY PURE, ADVANCED TRICYCLIC INTERMEDIATE FOR THE SYNTHESIS OF CEROPLASTERIC ACID

被引：14
|
作者：
RIGBY, JH
MCGUIRE, T
SENANAYAKE, C
KHEMANI, K
机构：
[1] Department of Chemistry, Wayne State University, Detroit
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期
关键词：
D O I：
10.1039/p19940003449
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tropone has been transformed into an optically pure tricyclic system that could serve as an advanced intermediate in the synthesis of ceroplasteric acid. The sequence features a stereoselective Ireland ester enolate Claisen rearrangement followed by an intramolecular nitrile oxide cycloaddition for assembly of an ABC-ring precursor of the target molecule. Efforts to homologate the seven-membered B ring to the requisite eight-membered system were unsuccessful.
引用
收藏
页码：3449 / 3457
页数：9
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