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11-Step Total Synthesis of Teleocidins B-1-B-4.

ABSTRACT: A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize concession steps, the tactical combination of C-H borylation and a Sigman-Heck transform enabled the convergent, stereocontrolled synthesis of the teleocidins.

SUBMITTER: Nakamura H

PROVIDER: S-EPMC6353666 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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11-Step Total Synthesis of Teleocidins B-1-B-4.

Nakamura Hugh H Yasui Kosuke K Kanda Yuzuru Y Baran Phil S PS

Journal of the American Chemical Society 20190115 4

A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize concession steps, the tactical combination of C-H borylation and a Sigman-Heck transform enabled th ...[more]

PMID: 30636411

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