Stereoselectivity of the Reduction of Naltrexone Oxime with Borane

Mosad S. Mohamed, Philip S. Portoghes

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

The opiate β-naltrexamine (lb)1,2 is employed as an intermediate in the synthesis of the affinity label β-funaltrexamine (2),3 which is employed widely as a tool in opioid research.4 A highly stereoselective synthesis of lb has been but its time-consuming nature prompted us to examine a simple alternative approach. In this report, we describe a simple stereoselective method for preparing lb. Moreover, this method may have general application in altering the usual stereochemical course of reductive amination in vicinally substituted cyclohexanones.

Original languageEnglish (US)
Pages (from-to)105-106
Number of pages2
JournalJournal of Organic Chemistry
Volume51
Issue number1
DOIs
StatePublished - 1986

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