Staurosporine and <i>ent</i>-Staurosporine: The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

Abstract

The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.