Total Synthesis of (−)-Cinatrin C<sub>1</sub> Based on an In(OTf)<sub>3</sub>‑Catalyzed Conia-Ene Reaction
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Abstract
The
stereocontrolled total synthesis of (−)-cinatrin C<sub>1</sub>, a phospholipase A<sub>2</sub> inhibitor, has been accomplished.
The key feature includes the stereoselective construction of the highly
substituted tetrahydrofuran core by In(OTf)<sub>3</sub>-catalyzed
Conia–ene reaction of the oxygen-tethered acetylenic malonic
ester followed by dihydroxylation with concomitant lactonization