4.7 Article

Total Synthesis of (-)-Cinatrin C1 Based on an In(OTf)3-Catalyzed Conia-Ene Reaction

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 8, Pages 3847-3857

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo400263w

Keywords

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Funding

  1. JSPS [22249001, 21790019]
  2. MEXT [2304, 24105526, 2105, 24106736]
  3. Research Foundation for Pharmaceutical Sciences
  4. Grants-in-Aid for Scientific Research [22249001, 24659009, 24106736, 25253002, 24105526, 21790019] Funding Source: KAKEN

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The stereocontrolled total synthesis of (-)-cinatrin C-1, a phospholipase A(2) inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)(3)-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.

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