Ring closing metathesis mediated synthesis of 4a-aryloxodecahydroisoquinolines, intermediates in the preparation of novel opiates.
[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.
Liras
S
S
Pfizer Global Research and Development, Groton, Connecticut 06340, USA. spiros_liras@groton.pfizer.com
Allen
M P
MP
Blake
J F
JF
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
D000475:Alkenes; D000701:Analgesics, Opioid; D001880:Boranes; D007202:Indicators and Reagents; D007546:Isoquinolines