New Highly Stereoselective Synthesis of (E)-Droloxifene via Selective Protection of 3, 4′-Dihydroxybenzophenone and McMurry Reaction

S Gauthier, JY Sancéau, J Mailhot, B Caron, J Cloutier

Index: Gauthier, Sylvain; Sanceau, Jean-Yves; Mailhot, Josee; Caron, Brigitte; Cloutier, Julie Tetrahedron, 2000 , vol. 56, # 5 p. 703 - 709

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Citation Number: 15

Abstract

A new, highly stereoselective synthesis of (E)-droloxifene is reported. Deprotection of 3, 4′- dimethoxybenzophenone and selective pivaloylation of the 3′-phenolic position gave 4- hydroxy-3′-(trimethylacetoxy) benzophenone. A McMurry reaction between the preceding benzophenone and propiophenone gave the (E)-olefin as a major product (14: 1 E/Z ratio in crude reaction), which was then alkylated with 2-dimethylaminoethyl chloride and ...