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Synthesis 2007(12): 1785-1796  
DOI: 10.1055/s-2007-983712
PAPER
© Georg Thieme Verlag Stuttgart · New York

Boron Trichloride Mediated Regioselective Claisen Rearrangement of Resorcinol­ Derivatives: Application to Resorcinol Carvonyl Ethers

Fumihiro Ito, Keiko Fusegi, Takuya Kumamoto*, Tsutomu Ishikawa
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Fax: +81(43)2902911; e-Mail: tkuma@p.chiba-u.ac.jp;
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Publication History

Received 1 March 2007
Publication Date:
08 June 2007 (online)

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Abstract

Claisen rearrangement (CR) of resorcinol allyl ethers was examined. Although thermal CR gave low regioselectivity, the selectivity was much improved in the presence of a Lewis acid such as boron trichloride. This rearrangement was successfully applied to resorcinol carvonyl ethers for the regioselective introduction of a carvone unit into the resorcinol skeleton for the synthesis of phytoestrogenic miroestrols.

Key words

carvone - boron trichloride - rearrangement - regioselectivity - resorcinol

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