Studies on lysergic acid diethylamide and related compounds. V. Syntheses of dihydrolysergic acid diethylamides and related compounds.

Abstract

Epimeric pairs of dihydrolysergic acid diethylamide and dihydroisolysergic acid diethylamide were synthesized by hydrogenation of lysergic acid diethylamide (LSD) and iso LSD. Lysergol was obtained by LAH reduction of methyl lysergate which was prepared by treatment of a solution of lysergic acid in HMPA with diazomethane. From lysergol, lysergine and isolysergine were prepared. Festuclavine, pyroclavine, and costaclavine were synthesized by reduction of agroclavine with metal sodium in butanol and their structures were chemically confirmed. ORD curves of these alkaloids were determined and discussed.