Application of the Mitsunobu Reaction for Morphine Compounds. Preparation of 6β-Aminomorphine and Codeine Derivatives

Abstract

By the application of the Mitsunobu reaction several new 7 8 6β-aminomorphine and codeine derivatives, carrying a Δ^7,8 double bond in ring C have been synthesized. The catalytic hydrogenation of these compounds offered a new stereoselective way for the synthesis of the corresponding 6β-amino-dihydro analogues. The different conformation of ring C of the saturated and unsaturated amino compounds allows to study the structure-activity relationship, and by tritiation of the unsaturated derivatives the substrate-receptor interactions can be examined.