Apomorphinans from Isoquinolines: Grewe cyclization of 1??(2??hydroxybenzyl)??N??methyloctahydroisoquinoline and its O??methyl ether

…, A Brossi, JL Flippen??Anderson, R Gilardi

Index: Schmidhammer, Helmut; Brossi, Arnold; Flippen-Anderson, Judith L.; Gilardi, Richard Helvetica Chimica Acta, 1983 , vol. 66, # 8 p. 2437 - 2442

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Citation Number: 2

Abstract

Abstract Wolff-Kishner reduction of the optically active ketomorphinan 5 afforded the optically active morphinan 6 differing chromatographically and spectroscopically from the material obtained in a Grewe-cyclization of the isoquinoline 1. A single crystal X-ray analysis of a hydrobromide salt of a phenolic amine obtained from 1 and 2 with refluxing hydrobromic acid showed this compound to be the N-methylapomorphinan 4.