Total synthesis of teleocidins B-1-B-4 by redox-relay chain walking (RRCW)

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Abstract

Teleocidine B family was isolated in1960 by Sakai group and was shown to have highly potent protein kinase-C (P K C) 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.

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Nakamura, H., Yasui, K., & Baran, P. S. (2021). Total synthesis of teleocidins B-1-B-4 by redox-relay chain walking (RRCW). Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 79(4), 333–343. https://doi.org/10.5059/yukigoseikyokaishi.79.333

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