Synthesis of scalaridine A

Abstract

A synthesis of the pyridine-linked bisindole alkaloid scalaridine A is described. An iridium catalyzed, directed C–H borylation of N-Boc-5-methoxyindole gave the corresponding 3-borylindole, which underwent a one-pot, double Suzuki–Miyaura cross-coupling reaction with 3,5-dibromopyridine to install the entire heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of scalaridine A, which was spectroscopically identical to that described in the isolation report.