Formal synthesis of (+)-sorangicin A

Org Lett. 2011 Sep 2;13(17):4712-5. doi: 10.1021/ol201920j. Epub 2011 Aug 11.

Abstract

The formal synthesis of (+)-sorangicin A was completed by two independent routes. Both approaches feature a cross metathesis reaction to form the C29-C30 bond to arrive at the bicyclic ether/tetrahydropyran fragment. Formation of the C15-C16 olefin to unite the dihydropyran fragment with the rest of the molecule was achieved by either a cross metathesis reaction or a Julia-Kocienski olefination.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aminoglycosides / chemical synthesis*
  • Aminoglycosides / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Aminoglycosides
  • sorangicin A