Biosynthesis of phenols. Part XIII. Structural relationships of alkaloids of Demerara greenheart

Abstract

The molecular structures of four alkaloids isolated from Demerara greenheart have been determined through degradation and the investigation of absorption spectra, optical rotatory dispersion, n.m.r. and, in particular, high resolution mass spectra. Three of the bases, rodiasine, ocotine, and ocotosine, are related bisbenzylisoquinolines with one diaryl ether and one biphenyl bridge. The fourth has been identified as 2-nor-(+)-tetrandine. The structural relationships of the compounds have been discussed.