A total synthesis of (+)-negamycin through isoxazolidine allylation

Org Biomol Chem. 2014 Jul 21;12(27):4879-84. doi: 10.1039/c4ob00537f.

Abstract

The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate. The key allylation reaction proceeded with complete trans-selectivity, which is attributed to electrostatic attraction between the chlorine atom and the iminium ion in the Sakurai intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids, Diamino / chemical synthesis
  • Anti-Bacterial Agents / chemical synthesis*
  • Isoxazoles / chemistry*
  • Static Electricity

Substances

  • Amino Acids, Diamino
  • Anti-Bacterial Agents
  • Isoxazoles
  • negamycin