Abstract

The structure of (+)-ethyl 3,18-dimethoxy-5β,17-dimethyl-4,5α-epoxy-6β,14β-ethenomorphinan-8β-carboxylate (3), C 25 H 31 NO 5 , is described. Diels-Alder reaction of the thebaine analogoue (-)-5β-methyl-7-methoxy-6-demethoxythebaine (2), with ethyl propenoate gives rise to anomalous α-face approach of the dienophile, yielding the title compound (3), in which the etheno bridge is at the 6β,14β position and the ethoxycarbonyl substituent is at the 8β position

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