Synthesis of polyether macrodiolides based on acetylenic derivatives of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid

The stereoselective synthesis of (5 Z ,9 Z )-tetradeca-5,9-diene-1,14-dioic acid was carried out using Ti-catalyzed homo -cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2 H -pyran. Intermolecular esterification of this dicarboxylic acid with polyether acetylenic alcohols in the presence o...

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Bibliographic Details
Published in:Russian chemical bulletin 2023-10, Vol.72 (10), p.2473-2483
Main Authors: Islamov, I. I., Yusupova, A. V., D’yakonov, V. A., Dzhemilev, U. M.
Format: Article
Language:English
Subjects:
Alcohols
Carbodiimides
Chemical bonds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dicarboxylic acids
Esterification
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Inorganic Chemistry
Organic Chemistry
Stereoselectivity
Synthesis
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Summary:The stereoselective synthesis of (5 Z ,9 Z )-tetradeca-5,9-diene-1,14-dioic acid was carried out using Ti-catalyzed homo -cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2 H -pyran. Intermolecular esterification of this dicarboxylic acid with polyether acetylenic alcohols in the presence of carbodiimides was used to synthesize the corresponding monoesters and symmetric diesters. Using the intramolecular oxidative coupling of terminal triple bonds of the latter compounds, polyether macrodiolides containing 1 Z ,5 Z -diene and 1,3-diyne fragments were synthesized.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-023-4049-x