Studies towards the synthesis of medermycin via Dötz benzannulation

Chirality. 2015 Jan;27(1):18-22. doi: 10.1002/chir.22383. Epub 2014 Oct 17.

Abstract

The C-arylglycosides are available in enantiomerically pure form via the Dötz benzannulation reaction between Fischer alkenyl chromium carbene complexes and alkynes; it also could be converted to a precursor of medermycin by O-carbamate directed ipso bromination and nitrile substitution in good overall yields.

Keywords: C-arylglycoside; Dötz benzannulation; Fischer carbene complex; Streptomyces sp; ipso bromination.

Publication types

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

MeSH terms

  • Molecular Structure
  • Naphthoquinones / chemical synthesis
  • Naphthoquinones / chemistry
  • Stereoisomerism

Substances

  • Naphthoquinones
  • medermycin