Total synthesis of (-)-cinatrin C1 based on an In(OTf)3-catalyzed Conia-Ene reaction

  • J Org Chem. 2013 Apr 19;78(8):3847-57. doi: 10.1021/jo400263w.
Fumiya Urabe  1 ,  Shunsuke Nagashima ,  Keisuke Takahashi ,  Jun Ishihara ,  Susumi Hatakeyama
Affiliations
  • 1. Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
PMID: 23578072 DOI: 10.1021/jo400263w
Abstract

The stereocontrolled total synthesis of (-)-cinatrin C1, a Phospholipase A2 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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