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Synthetic Approaches to Optically Active Macrolides Containing Hydrazide Fragments of L-(+)-Tartaric Acid from (+)-3-Carene, (+)-α-Pinene, and S-(–)-Limonene

Author:
Ishmuratov, G. Yu., Yakovleva, M. P., Shutova, M. A., Muslukhov, R. R., Ishmuratova, N. M., Tolstikov, A. G.
Source:
Chemistry of natural compounds 2014 v.50 no.4 pp. 658-660
ISSN:
0009-3130
Subject:
alpha-pinene, carene, chemical structure, hydrazides, macrolides, ozonolysis, tartaric acid
Abstract:
An optically pure macrolide containing 1,3-dioxolane, gem-dimethylcyclopropyl, and hydrazide fragments was synthesized from (+)-3-carene via [1+1]-condensation of the product from sequential ozonolysis—reduction and Tishchenko disproportionation of (3S,4S)-[(3R,4R)-4-isopropyl-3-methyl-6-oxoheptyl]-4-isopropyl-3-methyl-6-oxoheptanoate with the hydrazide of L-(+)-tartaric acid acetonide.
Agid:
819461