ALLENYL ETHERS AS PRECURSORS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND BOTRYODIPLODIN DERIVATIVES

被引：39

作者：

DULCERE, JP

MIHOUBI, MN

RODRIGUEZ, J

机构：

[1] Laboratoire de Synthèse Organique, URA, CNRS 1411, Faculté des Sciences et Techniques de St. Jérôme, 13397 Marseille Cédex 20, D12, Avenue Escadrille Normandie Niemen

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 21期

关键词：

D O I：

10.1021/jo00073a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beta-Bromopropargyl ethers 2a-h, 11, and 12 or allyl propargyl ethers 8d-h are easily isomerized with potassium tert-butoxide (KO-t-Bu) into the corresponding allenyl derivatives 3a-h, 13, 14, and 9d-h. These compounds afford alpha-methylene-gamma-butyrolactones 7a-h, 25, and 26 by application of the sequence halogenation/dehydrohalogenation/homolytic carbocyclization. Starting from methyl vinyl ketone 1i, similar transformations lead to botryodiplodin (27) or ethoxybotryodiplodin (28).

引用

页码：5709 / 5716

页数：8

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