Synthesis of (−)-Mitrephorone A via a Bioinspired Late Stage C–H Oxidation of (−)-Mitrephorone B | Zendy

Lukas A. Wein | Zendy; Klaus Wurst | Zendy; Péter Angyal | Zendy; Lara Weisheit | Zendy; Thomas Magauer | Zendy

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

Author(s) -

Lukas A. Wein,

Klaus Wurst,

Péter Angyal,

Lara Weisheit,

Thomas Magauer

Publication year - 2019

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.9b11646

Subject(s) - chemistry , oxetane , electrochemistry , combinatorial chemistry , catalysis , natural product , stereochemistry , organic chemistry , electrode

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.

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