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Paper | Regular issue | Vol 36, No. 9, 1993, pp.2087-2097
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6425
Diastereoselective Conjugate Addition Approach to Picenadol and Oxygenated Analogues

Michael J. Martinelli,* Barry C. Peterson, and Darrell R. Hutchison

*Lilly Reserach Laboratories, A Division of Eli Lilly & Company, Lilly Corporate Center, Indianapolis, IN 46285-4813, U.S.A.

Abstract

Horner-Emmons-Wadsworth reaction with 1,3-dimethyl-4-piperidone in water afforded and exocyclic enone, whith minimal deconjugation of the double bond. Copper catalyzed conjugate addition with an aryl Grignard reagent then afforded an adduct with high stereocontrol. Wolff-Kischner reduction and deprotection proceeded to provide picenadol (1) in excellent overall yield. Access to oxygenated analogues of picenadol was also accomplished with this approach.