A new rearrangement product of thebaine, isolated from Papaver bracteatum Lindl. Structural assignment of thebaine N-oxides

Abstract

From Papaver bracteatum an unusual alkaloid is isolated: 6,7,8,9,10,14-hexadehydro-4,5-epoxy-3,6-di-methoxy-17-methylthebinan (1). This alkaloid is also obtained from the mixture of rearrangement products of one of the thebaine N-oxides. The structure of another constituent of the latter mixture is deduced to be 6,7,8,9,10,14-hexadehydro-3,6-dimethoxythebinan-4-ol (15). The presence of both thebaine N-oxides in Papaver bracteatum is confirmed, and their structures are revised on chemical and spectroscopic grounds.