First Synthetic Macrocyclic Compounds in the Series of ent-Beyerane Diterpenoids

摘要

New macrocyclic compounds were synthesized by reaction of 16-hydroxy-ent-beyeran-19-oic acid(derivative of the diterpenoid isosteviol with reduced ketone group)with adipic,suberic,and sebacic acid chlorides.We previously[1]synthesized diesters III-V from diterpenoid isosteviol(I,ent-16-oxobeyeran-19-oic acid)and adipic,suberic,and sebacic acid chlorides.Analysis of the reaction mixtures by thin-layer chromatography revealed the presence of trace amounts of weakly polar products with R_f 0.9(diesters III-V had an R_f value of 0.7,petroleum ether-diethyl ether-benzene,1:1:1).