Synthesis of optically active macrolides bearing di- and triethylene glycol and dicarboxylic acid hydrazide moieties from (-)-α-pinene

Abstract

Six optically active macroheterocycles bearing ester and dihydrazide moieties were synthesized from available natural (-)-α-pinene through the intermediate keto acid, (3¹R,3³R)- 1-hydroxy-3²,3²-dimethyl-1,4-dioxopentaphane, using the [2+1] reaction of this keto acid with di- or triethylene glycols and the [1+1] condensation of the resulting α,ω-diketo diesters with dicarboxylic acid dihydrazides in the key steps.