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

页码：3449 / 3457

页数：9

共 39 条

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