Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.