DIASTEREOSELECTIVE CONJUGATE ADDITION APPROACH TO PICENADOL AND OXYGENATED ANALOGS

Authors
MARTINELLI MJ PETERSON BC HUTCHISON DR
Citation
Mj. Martinelli et al., DIASTEREOSELECTIVE CONJUGATE ADDITION APPROACH TO PICENADOL AND OXYGENATED ANALOGS, Heterocycles, 36(9), 1993, pp. 2087-2097
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
36
Issue
9
Year of publication
1993
Pages
2087 - 2097
Database
ISI
SICI code
0385-5414(1993)36:9<2087:DCAATP>2.0.ZU;2-E
Abstract
Horner-Emmons-Wadsworth reaction with 1,3-dimethyl-4-piperidone in wat er afforded an exocyclic enone, with minimal deconjugation of the doub le bond. Copper catalyzed conjugate addition with an aryl Grignard rea gent then afforded an adduct with high stereo control. Wolff-Kisch ner reduction and deprotection proceeded to provide picenadol (1) in exce llent overall yield. Access to oxygenated analogues of picenadol was a lso accomplished with this approach.