Synthesis of spiro[5.4]decenones and their transformation into bicyclo[4.4]deca-1,4-dien-3-ones by domino "elimination- double-Wagner-Meerwein-rearrangement" reactions.

作者信息

Bose Gopal, Ullah Ehsan, Langer Peter

机构信息

Institut für Chemie und Biochemie der Ernst-Moritz-Arndt Universität Greifswald, Soldmannstrasse 16, 17487 Greifswald, Germany.

出版信息

Chemistry. 2004 Nov 19;10(23):6015-28. doi: 10.1002/chem.200400707.

The [3+3] cyclization of 1,3-bis-silyl enol ethers with 1,1-diacylcyclopentanes allows a convenient synthesis of spiro[5.4]decenones. Treatment of these compounds with trifluoroacetic acid (TFA) afforded a great variety of bicyclo[4.4.0]deca-1,4-dien-3-ones containing an angular alkyl group. This core structure occurs in a number of pharmacologically relevant natural products.