Chapter 2 The Morphine Alkaloids

Abstract

Publisher Summary The morphinans represent a large group of alkaloids, related to the isoquinoline alkaloids. This chapter explores that the first representative of the morphinan group of alkaloids, morphine, was discovered 200 years ago. Many significant advances have been made in the isolation, structure elucidation, and chemistry of the morphinan alkaloids. The chapter focuses on the occurrence, isolation, structure elucidation, synthesis, transformations, reactions, biogenesis, and pharmacological activity of morphinan alkaloids. It discusses that because of the great medicinal importance of the morphinan alkaloids, as well as of codeine and semisynthetic derivatives, intensive research has been directed toward finding an effective and commercially feasible total synthesis for these compounds. The chapter also reviews that the biogenesis of morphine alkaloids has been the subject of numerous studies. Finally, it discusses conversion of the dihydrothebainone product of Grewe cyclization to codeine and morphine; the transformation of the biomimetic intermediate salutaridine and its derivatives; and semisynthetic approaches resulting in 14-hydroxy morphinan derivatives with high medicinal importance.