cis-decalins from quinic acid: toward a synthesis of branimycin

Org Lett. 2007 Mar 1;9(5):813-6. doi: 10.1021/ol0630189. Epub 2007 Feb 1.

Abstract

[reaction: see text] Starting from (-)-quinic acid an efficient synthesis of highly functionalized cis-alpha,beta-unsaturated ketone 3, an advanced precursor of branimycin, has been accomplished via two key step reactions: a ring closing metathesis reaction to prepare the cis-decalin system, and a highly stereoselective epoxidation reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epoxy Compounds / chemistry
  • Ketones / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Models, Molecular
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Quinic Acid / chemistry*

Substances

  • Epoxy Compounds
  • Ketones
  • Macrolides
  • Naphthalenes
  • branimycin
  • Quinic Acid
  • decalin