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Paper | Regular issue | Vol 32, No. 12, 1991, pp.2381-2388
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5855
10,11-Epoxy-3-methyl-1,2,3,4-tetrahydro-4a,10b-propanobenzo[f]isoquinolin-12-ones: A Novel Type of Opioid Analgesics — Synthetic Approach and Structure Elucidation

Martin Kratzel* and Horst Völlenkle

*Institut für Pharmazeutische Chemie, Universität Wien , Pharmaziezentrum, Althanstraβe, 10 A-1090 Wien, Austria


The title compounds were obtained by nucleophilic cyclopropane ring opening and intramolecular Hofmann reactions, starting from 7,14-cyclodihydrocodeinone (1). An X-ray analysis of 10,11-epoxy-9-methoxy-3-methyl-1,2,3,4-tetrahydro-4a,10b-propanobenzo[f]isoquinolin-12-one dimethyl acetal (3) was performed as basis of molecular modeling studies.