Work

A Novel Divergent Synthesis of ortho-Hydroxy-E and -F Oxide-Bridged 5-Phenylmorphans

Year: 2007

Type: article

Abstract: 5-(2-Bromo-3-methoxyphenyl)-2-methyl-2-azabicyclo[3.3.1] nonan-9-one was prepared in six steps from a known phenylacetonitrile. Stereoselective reduction of the ketone furnished the corresponding (3- 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.

Source: Heterocycles

DOI: 10.3987/com-07-11000

Authors: Kenner C. Rice, Josef Zezula, Arthur E. Jacobson

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

OpenAlex ID: W2949911408

FWCI: 1.253

Cites: 3

Cited by: 12

Related to: 10