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Paper | Regular issue | Vol 71, No. 4, 2007, pp.881-889
Published online, 9th February, 2007
DOI: 10.3987/COM-07-11000
A Novel Divergent Synthesis of ortho-Hydroxy-E and -F Oxide-Bridged 5-Phenylmorphans

Josef Zezula, Arthur E. Jacobson, and Kenner C. Rice*

*Drug Design and Synthesis Section, Chemical Biology Research Branch, Building 8, Room B1-23, National Institute on Drug Abuse, National Institutes of Health, Department of Health and Human Services, Bethesda, Maryland, 20892-0815, USA


5-(2-Bromo-3-methoxyphenyl)-2-methyl-2-azabicyclo[3.3.1]nonan-9-one was prepared in six steps from a known acetonitrile. Stereoselective reduction of the ketone furnished the corresponding β- or α-alcohols and their deprotonation, intramolecular cyclization, and demethylation gave ortho-hydroxy-e and -f oxide-bridged 5-phenylmorphans, respectively. This new synthetic route has the desired oxygenation pattern in place, eliminating the problematic diazonium reactions used in former syntheses.