Open AccessSynthesis of (−)-Mitrephorone A via a Bioinspired Late Stage C–H Oxidation of (−)-Mitrephorone B
Author(s) -
Lukas Anton 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.