An efficient and convenient formal synthesis of Jaspine B from d-xylose

A formal synthesis of Jaspine B was completed in 42.4% overall yield with only three purification steps (one by crystallization and two by column chromatography). The key step in the synthesis involves a regio- and stereoselective epoxide ring-opening reaction and the configuration inversion of the C3-hydroxyl group through oxidation and reduction. All of the reagents and materials used were quite common and inexpensive.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide