NMR Analysis of a Series of 6,14-Ethenomorphinan Derivatives as PET Precursors and Reference Substances

摘要

The new semisynthetic oripavine derivative 3-O-trityl-6-O-desmethyl-dihydroetorphine was synthesized from the poppy alkaloid thebaine in a six-step procedure. This compound can be applied as precursor for the radiosynthesis of [6-O-meth-yl-~(11)C]-dihydroetorphine ([~(11)C]DHE). We present a detailed description of 1H and ~(13)C NMR data of reference standards and precursors for [6-O-methyl-~(11)C]- and [6-O-(2-[~(18)F]fluoroethyl] orvinols. This includes the complete assignment for 19 oripavine derivatives examined in 1D and 2DNMR experiments. We also investigated the molecular basis for regioselectivity of fluoroalkylation of 3-O-trityl-6-O-desmethyl-phenethyl-orvinol (TDPEO) using computational methods.