Synthesis

Boron trichloride mediated regioselective claisen rearrangement of resorcinol derivatives: Application to resorcinol carvonyl ethers

F Ito, K Fusegi, T Kumamoto, T Ishikawa

Index: Ito, Fumihiro; Fusegi, Keiko; Kumamoto, Takuya; Ishikawa, Tsutomu Synthesis, 2007 , # 12 p. 1785 - 1796

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Citation Number: 8

Abstract

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.