We present a bioinspired late-stage C-H oxidation of the -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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6946608 | PMC |
| http://dx.doi.org/10.1021/jacs.9b11646 | DOI Listing |
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Synthesis of (-)-Mitrephorone A via a Bioinspired Late Stage C-H Oxidation of (-)-Mitrephorone B.
J Am Chem Soc
December 2019
Institute of Organic Chemistry and Center for Molecular Biosciences , Leopold-Franzens-University Innsbruck, Innrain 80-82 , 6020 Innsbruck , Austria.
We present a bioinspired late-stage C-H oxidation of the -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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