A NOVEL DIVERGENT SYNTHESIS OF ORTHO-HYDROXY-E AND-F OXIDE-BRIDGED 5-PHENYLMORPHANS

摘要

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 beta-or alpha-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.