A Stereoselective Synthesis of Nonracemic (+)-Desoxoprosophylline by a Tandem Wittig [2+3]-Cycloaddition Reaction

Abstract

L-Ascorbic acid serves as chiral starting material for the synthesis of (+)-desoxoprosophylline. The synthetic pathway includes the formation of an O-protected 5-azido-2,3-dideoxysugar which is subjected to a tandem Wittig [2+3]-cycloaddition reaction, leading to the heterocyclic core unit of (+)-prosophylline. Stereoselective hydrogenation and chain elongation yields the desired alkaloid.