Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling

Org Lett. 2018 Sep 21;20(18):5554-5558. doi: 10.1021/acs.orglett.8b02183. Epub 2018 Sep 12.

Abstract

The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key step, enabled generation of the axial chirality.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Molecular Conformation
  • Oxidative Coupling
  • Phenols / chemistry*
  • Vanadium / chemistry*

Substances

  • Isoquinolines
  • Phenols
  • chaetoglobin A
  • Vanadium