This article is cited in 11 papers

Communications

Stereoselective synthesis and antitumor activity of macrodiolides containing 1Z,5Z-diene and 1,3-diyne moieties

V. A. D'yakonov, I. I. Islamov, L. U. Dzhemileva, M. M. Yunusbaeva, U. M. Dzhemilev

Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: New macrodiolides incorporating 1Z,5Z-diene and 1,3-diyne moieties were obtained in 55–79% yields and with >98% stereoselectivity by Hf(OTf)₄-catalyzed intermolecular cyclocondesation of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid with a,ω-diols. Alternative route included intramolecular oxidative coupling of a,ω-diynes, esterification products of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid with alkynols. The macrodiolides synthesized exhibit in vitro cytotoxic activity toward Jurkat, K562, U937, HL-60, HeLa and Hek293 cell lines.

Language: English

DOI: 10.1016/j.mencom.2019.11.002

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