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Synthesis of (-)-Mitrephorone A via a Bioinspired Late Stage C-H Oxidation of (-)-Mitrephorone B.

ABSTRACT: We present a bioinspired late-stage C-H oxidation of the ent-trachylobane natural product mitrephorone B to mitrephorone A. The realization of this unprecedented transformation was accomplished by either an iron-catalyzed or electrochemical oxidation and enabled access to the densely substituted oxetane in one step. Formation of mitrephorone C, which is lacking the central oxetane unit but features a keto-function at C2, was not formed under these conditions.

SUBMITTER: Wein LA

PROVIDER: S-EPMC6946608 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Synthesis of (-)-Mitrephorone A via a Bioinspired Late Stage C-H Oxidation of (-)-Mitrephorone B.

Wein Lukas Anton LA Wurst Klaus K Angyal Peter P Weisheit Lara L Magauer Thomas T

Journal of the American Chemical Society 20191203 50

We present a bioinspired late-stage C-H oxidation of the <i>ent</i>-trachylobane natural product mitrephorone B to mitrephorone A. The realization of this unprecedented transformation was accomplished by either an iron-catalyzed or electrochemical oxidation and enabled access to the densely substituted oxetane in one step. Formation of mitrephorone C, which is lacking the central oxetane unit but features a keto-function at C2, was not formed under these conditions. ...[more]

PMID: 31770485

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