Tetrahedron Letters

A concise, stereoselective synthesis of picenadol

MJ Martinelli, BC Peterson

Index: Martinelli, Michael J.; Peterson, Barry C. Tetrahedron Letters, 1990 , vol. 31, # 38 p. 5401 - 5404

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Citation Number: 2

Abstract

Abstract A four-step stereoselective synthesis of picenadol (1) is reported, 1, 3-Dimethyl-4- piperidone (3) underwent Horner-Wadsworth-Emmons reaction under conditions that did not yield double-bond isomerization, followed by a directed 1, 4-addition with an aryl cuprate. Reduction and deprotection then afforded (1).