Synthesis and Structure of Drimane Sesquiterpenoids Containing Pyrimidine, Pyrazine, 1,2,4-triazole, and Carbazole Rings

摘要

Drimenic acid was synthesized in six steps from norambreinolide. Reaction of drimenic acid with oxalyl chloride produced iso-drimenic acid chloride, which reacted with heterocyclic amines (2-aminopyrimidine, 2-aminopyrazine, 4-aminopyrimidine, N-aminocarbazole, and 3-amino-1,2,4-triazole) to form amides of iso-drimenic and albicanic acids. The structures of the amides were elucidated by spectral methods and an X-ray structure analysis.