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

J Am Chem Soc. 2019 Dec 18;141(50):19589-19593. doi: 10.1021/jacs.9b11646. Epub 2019 Dec 3.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetics*
  • Carbon / chemistry*
  • Chemistry Techniques, Synthetic
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Hydrogen / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Oxidation-Reduction

Substances

  • Diterpenes
  • mitrephorone A
  • mitrephorone B
  • Carbon
  • Hydrogen