Synthesis of Optically Active Macrolides from L-menthol

Effective syntheses of three optically active macroheterocycles with ester, azine, and dihydrazide fragments were developed from available natural L-menthol through intermediate 3R,7-dimethyl-6-oxooctanoic acid using [2 + 1]-reaction of the last with diethylene glycol and [1 + 1]-condensation of the...

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Bibliographic Details
Published in:Chemistry of natural compounds 2018-09, Vol.54 (5), p.889-892
Main Authors: Yakovleva, M. P., Mingaleeva, G. R., Denisova, K. S., Ishmuratova, N. M., Ishmuratov, G. Yu
Format: Article
Language:English
Subjects:
Antiviral agents
Dicarboxylic acids
Hydrazines
Infrared spectroscopy
Medicine
Menthol
NMR spectroscopy
Nuclear magnetic resonance spectroscopy
Optical activity
Organic Chemistry
Oxazoles
Pharmacy
Plant Sciences
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Summary:Effective syntheses of three optically active macroheterocycles with ester, azine, and dihydrazide fragments were developed from available natural L-menthol through intermediate 3R,7-dimethyl-6-oxooctanoic acid using [2 + 1]-reaction of the last with diethylene glycol and [1 + 1]-condensation of the resulting α,ω-diketodiester with hydrazine hydrate and dihydrazides of several dicarboxylic acids in the key steps. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and GC-MS.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-018-2505-x