Stereospecific synthesis of hexahydrobenzopyrroloisoquinoline and tetrahydrobenzisoquinoline derivatives

Abstract

New optically active hexahydrobenzopyrroloisoquinoline and tetrahydrobenzisoquinoline derivatives have been synthesized. Metal hydride reduction of the cyclic amino ketones, prepared by mild Friedel-Crafts type intramolecular acylation of N-naphthalenylmethyl amino acids, yielded pairs of diastereoisomeric alcohols. The absolute stereochemistry and some features of the n.m.r. spectra of hexahydrobenzopyrroloisoquinolines, tetrahydrobenzisoquinoline and those of their intermediates are discussed.