title: Ring closing metathesis mediated synthesis of 4a-aryloxodecahydroisoquinolines, intermediates in the preparation of novel opiates.
abstract: [reaction: see text]. The concise syntheses of the 4a-aryldecahydroisoquinolines 1 and 2 through a uniform strategy starting from N-methyl-3-allyl-4-piperidinone are reported in this Letter. Key transformations include a ring closing metathesis reaction to prepare a trans-octahydroisoquinoline common intermediate and a regiocontrolled hydroboration-oxidation sequence.
authors.affiliation: Pfizer Global Research and Development, Groton, Connecticut 06340, USA. spiros_liras@groton.pfizer.com
authors.forename: S
authors.initials: S
authors.lastname: Liras
authors.forename: M P
authors.initials: MP
authors.lastname: Allen
authors.forename: J F
authors.initials: JF
authors.lastname: Blake
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D001880:Boranes; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis*; D008958:Models, Molecular; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000701:Analgesics, Opioid; D001880:Boranes; D007202:Indicators and Reagents; D007546:Isoquinolines