Please login first
Synthesis of New Unsaturated Polyether Macrodiolides Based on the (7Z,11Z)-Octadeca-7,11-diene-1,18-dioic Acid
* 1 , 2 , 3
1  Institute of Petrochemistry and Catalysis of RAS
2  Institute of Petrochemistry and Catalysis, Russian Academy of Sciences
3  N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Academic Editor: Julio A. Seijas


Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using reaction Ti-catalyzed homo-cyclomagnesiation of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. By intermolecular esterification of dicarboxylic acid with polyether acetylene alcohols in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67-75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric 1Z,5Z-diene fragments in their structure were synthesized for the first time.

Keywords: Homo-cyclomagnesiation; 1,5-Dienoic compounds; Oxidative coupling; 1,3-Diynes; Macrodiolides