Journal of Organic Chemistry 2013-04-19

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

Fumiya Urabe, Shunsuke Nagashima, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama

Index: J. Org. Chem. 78(8) , 3847-57, (2013)

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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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