Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis

J Am Chem Soc. 2011 Oct 19;133(41):16418-21. doi: 10.1021/ja207835w. Epub 2011 Sep 23.

Abstract

The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Pyridines / chemistry*
  • Stereoisomerism
  • Streptonigrin / chemical synthesis*
  • Streptonigrin / chemistry

Substances

  • Pyridines
  • Streptonigrin
  • pyridine