Synthetic studies on phloroglucins: a new approach to the bicyclo[3.3.1]nonane system via the regioselective ring-opening of the methoxycyclopropane

被引：26
作者：
Abe, Masahito [1 ]
Nakada, Masahisa [1 ]
机构：
[1] Waseda Univ, Fac Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 28期
关键词：
D O I：
10.1016/j.tetlet.2007.05.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic approach to the bicyclo[3.3.1]nonane system, a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed. The key step in our approach is a 'one-pot' procedure of two successive reactions, the intramolecular cyclopropanation reaction which affords the tricyclo[4.4.0.0(5.7)]dec-2-ene derivative and its methoxy group directed regioselective ring-opening reaction mediated by ZnCl2, producing the desired bicyclo[3.3.1]nonane as the sole product. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4873 / 4877
页数：5
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