A [3+2] nitrile oxide intermolecular cycloaddition approach to 4,5-dihydro-3(2H)-furanone and 3(2H)-furanone ring systems: application to the formal synthesis of (±)-ascofuranone and geiparvarin.

Abstract

A unified approach to both 4,5-dihydro-3(2H)-furanone and 3(2H)-furanone rings systems centered on a [3+2] nitrile oxide cycloaddition strategy as a tool for the crucial carbon-carbon bond forming step has been successfully applied to the formal synthesis of )(±)-ascofuranone and to a new synthesis of geiparvarin from common intermediates.