Tricyclic Analogs of the Prodines

Abstract

A search for an analgesic with the potency of β-prodine and with the quality of analgesia associated with the benzomorphans led to the preparation of the octahydrobenz[f] isoquinoline system, a system where β-prodine is bridged in a manner related to the benzomorphans. Three different syntheses of this system are described. They permit access to a variety of substitution patterns as well as to the possible stereoisomers. The hybrid β-prodine-benzomorphan system displayed interesting CNS activity.