Design and Implementation of an Efficient Synthetic Approach to Pyranosylated Indolocarbazoles: Total Synthesis of (+)-RK286c, (+)-MLR-52, (+)-Staurosporine, and (−)-TAN-1030a

Abstract

A total synthesis of the natural products (+)-staurosporine (2), (+)-RK286c (3), (−)-TAN-1030a (4), and (+)-MLR-52 (5) has been achieved. The synthetic strategy involves the stereoselective ring expansion of a furanosylated indolocarbazole [(+)-8] to a pyranosylated congener [(+)-12] that serves as a common intermediate in the production of 2−5.