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The first total synthesis of natural acetogenin, chatenaytrienin-1, was performed in 10 steps and in 41% overall yield using cross-cyclomagnesiation of (6 Z )-heptadeca-1,2,6-triene and trideca-11,12-dien-1-ol tetrahydropyran acetal with EtMgBr in the presence of Mg metal and the Cp 2 TiCl 2 catalyst (10 mol %) as the key step of the synthesis.

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Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1