NEW TECHNOLOGY FOR THE CONSTRUCTION OF BICYCLO[6.2.1] RING-SYSTEMS

被引：24

作者：

WANG, WB ^{[1
]}

ROSKAMP, EJ ^{[1
]}

机构：

[1] NORTHWESTERN UNIV, DEPT CHEM, EVANSTON, IL 60208 USA

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 50期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(93)88002-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three new methods are presented in this synthesis of an 11-oxabicyclo[6.2.1]-undec-1,5,9-triene. They include: (1) the preparation of the dianion of 3-hydroxy-1,4-pentadiene; (2) an intramolecular Diels-Alder reaction accelerated by silica gel saturated with water; and (3) a tandem Grob fragmentation and homoallylic elimination of a cyclic sulfate. Overall, the synthesis of (1E, 5E, 9Z)-2-(t-Butyldimetbylsiloxy)-8-methyl-11-oxabicyclo[6.2.1]-undec-1,5,9-triene (1) was completed in 9 steps starting from 5-methylfurfural.

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页码：7631 / 7634

页数：4

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