Unified total synthesis of eburnamine-vincamine indole alkaloids based on catalytic asymmetric hydrogenation/lactamization cascade

Abstract

The enantioselective total synthesis of representative members of the eburnamine-vincamine alkaloids (+)-vincamine, (−)-eburnamonine, and (−)-criocerine has been accomplished. The synthesis took advantage of a highly stereoselective Ir-catalyzed hydrogenation/lactamization cascade reaction, which allows for the stereoselective construction of the C/D rings as well as the installation of the critical cis-C20/C21 relative stereochemistry of the eburnamine-vincamine alkaloid skeleton in one pot.

Keywords

• Indole alkaloid
• Imine
• Asymmetric hydrogenation
• Natural product
• Enantioselective synthesis