Tetrahedron Letters

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

Y Takashima, Y Kobayashi

文献索引：Takashima, Yuji; Kobayashi, Yuichi Tetrahedron Letters, 2008 , vol. 49, # 35 p. 5156 - 5158

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被引用次数: 12

摘要

Allylic substitution of allylic picolinate 5 with a copper reagent derived from p- MeOC6H4MgBr (6) and CuBr· Me2S produced the anti SN2′ 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).