Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory Activity

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Abstract
Convergent total syntheses of murisolin (1), natural 16,19-cis-murisolin 2, and unnatural 16,19-cis-murisolin 3 were accomplished by asymmetric alkynylation of α-tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ-lactone segment as the key steps. Stereoisomers of α-tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6-heptadiyne proceeded in good yield and with high diastereoselectivity. The cell-growth inhibition profile and COMPARE analysis of the synthetic compounds 1–3 were also investigated.