New synthetic route to (S)-(-)-equol through allylic substitution

Allylic substitution of allylic picolinate 5 with a copper reagent derived from p-MeOC6H4MgBr (6) and CuBr-Me2S produced the anti S(N)2' product 7 with high regioselectivity and efficient chirality transfer. Oxidative cleavage of the olefinic function to the alcohol followed by bromination afforded bromide 16, which upon demethylation and intramolecular ether ring formation furnished (S)-(-)-equol (3). (C) 2008 Elsevier Ltd. All rights reserved.