Abstract
Horner-Emmons-Wadsworth reaction with 1,3-dimethyl-4-piperidone in water afforded an exocyclic enone, with 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
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