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

页码：4873 / 4877

页数：5