Synthesis of versatile bicyclo[5.4.0]undecane systems from tetrachlorocyclopropene

被引：10

作者：

Batson, WA ^{[1
]}

Abboud, KA ^{[1
]}

Battiste, MA ^{[1
]}

Wright, DL ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 10期

基金：

美国国家科学基金会;

关键词：

tetrachlorocyclopropene; furan; Robinson annulation; bicyclo[5.4.0]undecane;

D O I：

10.1016/j.tetlet.2004.01.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,2,3.4-Tetrachloro-8-oxabicyclo[3.2.2]octa-2,6-diene, derived in a single step from the cyclocondensation of furan and tetrachlorocylopropene, serves as a key intermediate for the construction of bicyclo[5.4.0]undecane synthons. Conversion to a meso-1,3 diketone is followed by a high yielding Robinson annulation reaction. Studies on the reduction of the enone product reveals a powerful preference for formation of the cis-ring fusion. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2093 / 2096

页数：4

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