SYNTHESIS OF 5-HYDROXY-1,7-DIOXASPIRO[5.5]UNDEC-3-EN-2-ONES FROM 2-BENZENESULFONYLTETRAHYDROPYRANS AND 5-HYDROXYBUTENOLIDES - X-RAY CRYSTAL-STRUCTURE DETERMINATION FOR (5RS,6SR)-5-ACETOXY-4-METHOXY-3-METHYL-1,7-DIOXASPIRO[5.5]UNDEC-3-EN-2-ONE

被引：8

作者：

BAYLIS, AM ^{[1
]}

HELLIWELL, M ^{[1
]}

REGAN, AC ^{[1
]}

THOMAS, EJ ^{[1
]}

机构：

[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 04期

关键词：

D O I：

10.1039/p19930000411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-en-2-ones are obtained from reactions between 2-lithiated 2-benzenesulfonyltetrahydropyrans and 5-hydroxybutenolides. The structure of (5RS,6SR)-5-acetoxy-4-methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-3-en-2-one 16 was confirmed by X-ray crystallography. Addition of 5-lithiated 2,3-dihydrofuran and 6-lithiated 3,4-dihydro-2H-pyran to the hydroxybutenolide 12 gave the butenolides 30 and 31. Hydrolysis of 31 gave 33, which on dehydration returned 31 rather the conjugated isomer 32.

引用

页码：411 / 416

页数：6

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