Intramolecular Diels–Alder/Tsuji Allylation assembly of the functionalized trans-Decalin of Salvinorin A and sea lamprey migratory pheromone structure activity relationship studies.

Abstract

In the first portion of this work, an intramolecular Diels–Alder/Tsuji allylation assembly of functionalized trans-decalin systems will be discussed (Chapter I). This is presented in the context of synthetic studies toward the psychoactive (κ-opioid agonist) natural product salvinorin A. Synthetic studies of the sea lamprey (Petromyzon marinus) migratory pheromone will be discussed in Chapter II. In the third chapter, a structure activity relationship study of the sea lamprey migratory pheromone will be presented in which results suggest that the sea lamprey olfactory system is not uniquely and specifically recognizing the allo (i.e., 5α-H) configuration in bile acid derivatives.