Total Synthesis of Teleocidins B-1-B-4 by Redox-Relay Chain Walking (RRCW)

Abstract

Teleocidine B family was isolated in1960 by Sakai group and was shown to have highly potent protein kinase-C (PKC) activation, similar to that of phorbol and related natural products. In this report, we have developed a unified total synthesis of teleocidins B-1-B-4 in 11 chemical steps. The highlights of the work are 1) the Ni catalyzed electrochemical amination, 2) Cu-mediated aziridine opening followed by direct macrolactamization, and 3) the tactical combination of C-H borylation and a redox-relay chain walking (RRCW) methodology to make the carbon quaternary center.