| Summary: | Efficient methods have been developed for synthesizing previously unknown macrodiolides incorporating 1<i>Z</i>,5<i>Z</i>-diene and 1,3-diyne moieties in 54–84% yields and with >98% stereoselectivity by means of the intermolecular cyclocondesation of (7<i>Z</i>,11<i>Z</i>)-octadeca-7,11-dienedioic acid with α,ω-diols catalyzed by hafnium triflate Hf(OTf)<sub>4</sub> as well as via the oxidative coupling of α,ω-diynes obtained by the esterification of (7<i>Z</i>,11<i>Z</i>)-octadeca-7,11-dienedioic acid with alkynols. The synthesized macrodiolides exhibit cytotoxic activity toward the Jurkat, K562, U937, HL-60, HeLa, and Hek293 cell lines in vitro.
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