Journal
TETRAHEDRON
Volume 74, Issue 35, Pages 4606-4612Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.07.031
Keywords
Macrodiolides; 1,5-Dienoic compounds; 1,2-Dienes; Cyclomagnesiation; Homogeneous catalysis; Anti-cancer activity
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Funding
- Russian Science Foundation [17-73-10136]
- Russian Science Foundation
- Russian Science Foundation [17-73-10136] Funding Source: Russian Science Foundation
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An original strategy has been developed for the synthesis of valuable unsaturated macrocyclic lactones, macrodiolides, containing a 1Z,5Z-diene moiety in 57-79% yields and >98% stereoselectivity by hafnium triflate Hf(OTf)(4)-catalyzed intermolecular esterification of aliphatic alpha,omega-dicarboxylic acids with alpha,omega-alka-nZ,(n+4)Z-dienediols (1,12-dodeca-4Z,8Z-dienediol, 1,14-tetradeca-5Z,9Z-dienediol, 1,18-octadeca-7Z,11Z-dienediol). The diols were obtained by homo-cyclomagnesiation of tetrahydropyran ethers of oxygenated 1,2-dienes with EtMgBr in the presence of Mg metal and Cp2TiCl2 catalyst (10 mol. %). The resulting macrodiolides exhibit high cytotoxic activity in vitro against Jurkat, K562, U937, Hek293 and HeLa tumor cell lines. (C) 2018 Elsevier Ltd. All rights reserved.
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