4.6 Article

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

Journal

ACS OMEGA
Volume 4, Issue 9, Pages 14085-14091

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acsomega.9b01951

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Funding

  1. Russian Science Foundation [18-73-10030]
  2. Russian Science Foundation [18-73-10030] Funding Source: Russian Science Foundation

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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 (6Z)-heptadeca-1,2,6-triene and trideca-11,12-dien-1-ol tetrahydropyran acetal with EtMgBr in the presence of Mg metal and the Cp2TiCl2 catalyst (10 mol %) as the key step of the synthesis.

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