Arylamine-Mediated Construction of 1,2- cis C -Vinyl Furanosides and Application in the Synthesis of Jaspine B

Abstract

We report a two-step procedure for the synthesis of 1,2-cisC-vinyl furanosides from unprotected carbohydrates via an arylamine-mediated Petasis reaction and Brønsted acid-catalyzed deaminative cyclization. The method shows broad scope and high stereoselectivity. Its utility is demonstrated in a concise synthesis of Jaspine B, enabling the rapid assembly of the all-cis THF core. The late-stage amino installation is achieved via a radical-mediated C–H amidation reaction. The procedure provides practical access to bioactive THF-containing molecules.