Journal of the American Chemical Society, Vol.118, No.12, 2825-2842, 1996
Staurosporine and ENT-Staurosporine - The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles
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.
Keywords:PROTEIN-KINASE-C;INDOLE ALKALOID STAUROSPORINONE;DNA TOPOISOMERASE-I;PHYSICOCHEMICAL PROPERTIES;SIGNAL TRANSDUCTION;POTENT INHIBITOR;MICROBIAL ORIGIN;ARCYRIAFLAVIN-B;DERIVATIVES;INDOLE-2;3-QUINODIMETHANES