Toward more "ideal" polyketide natural product synthesis: a step-economical synthesis of zincophorin methyl ester

J Am Chem Soc. 2011 May 18;133(19):7308-11. doi: 10.1021/ja201467z. Epub 2011 Apr 27.

Abstract

A highly efficient and step-economical synthesis of zincophorin methyl ester has been achieved. The unprecedented step economy of this zincophorin synthesis is principally due to an application of the tandem silylformylation-crotylsilylation/Tamao oxidation-diastereoselective tautomerization reaction, which achieves in a single step what would typically require a significant multistep sequence.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / economics*
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Biological Products
  • Carboxylic Acids
  • Macrolides
  • zincophorin methyl ester