CYCLOADDITION OF C,N-DIARYLNITRONES TO 2-BUTENOLIDE - SYNTHESIS OF 2,3,6,6A-TETRAHYDROFURO[3,4-D]ISOXAZOL-4(3AH)-ONE

被引:25
作者
BANERJI, A
BASU, S
机构
[1] Centre of Advanced Studies on Natural Products, Department of Chemistry, Calcutta University, Calcutta, 700 009, 92, Acharya Prafulla Chandra Road
关键词
D O I
10.1016/0040-4020(92)85009-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cycloadditions of four C,N-diaryl nitrones (1-4) to the 5-membered conjugated lactone 2-butenolide were investigated. Two stereoisomeric 2-phenyl-3-aryl-2,3,6,6a-tetrahydrofuro[3,4-d]-isoxazol-4(3aH)-one cycloadducts and a ring-opened butanolide derivative were obtained in each case. The structure and stereochemistry of the products were determined by detailed NMR studies. The regiochemical course of the cycloadditions is explained, and the genesis of the ring-opened product rationalised.
引用
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页码:3335 / 3344
页数:10
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