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
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).
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页码:5709 / 5716
页数:8
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