Synthesis of New Morphinan Opioids by TBADT-Catalyzed Photochemical Functionalization at the Carbon Skeleton

Abstract

The synthesis of new morphinan opioids by the addition of photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring, is described. Using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer photocatalyst, diverse radical donors can be used to prepare a variety of C8-functionalized morphinan opioids. This work demonstrates the late-stage modification of complex, highly functionalized substrates.

Keywords: late-stage functionalization; morphinans; opioids; photocatalysis; radical reactions.