A concise total synthesis of puberulic acid, a potent antimalarial agent

Chem Commun (Camb). 2014 Aug 14;50(63):8715-8. doi: 10.1039/c4cc03134b. Epub 2014 Jun 25.

Abstract

Efficient and practical total synthesis of puberulic acid has been accomplished via 8 steps, with 54% overall yield, and only two C-C bond formations, without the introduction of oxygen atoms into the core skeleton. Construction of the tropolone framework as the key transformation was achieved by multi-tandem oxidation of the aliphatic-triol, from D-(+)-galactose as the starting material.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Carboxylic Acids / chemical synthesis*
  • Indicators and Reagents
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Penicillium / chemistry
  • Tropolone / analogs & derivatives*
  • Tropolone / chemical synthesis
  • Tropolone / chemistry

Substances

  • Antimalarials
  • Carboxylic Acids
  • Indicators and Reagents
  • puberulic acid
  • Tropolone
  • Oxygen