Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester

J Am Chem Soc. 2015 Jul 22;137(28):8900-3. doi: 10.1021/jacs.5b05296. Epub 2015 Jul 13.

Abstract

(+)-Zincophorin methyl ester is prepared in 13 steps (longest linear sequence). A bidirectional redox-triggered double anti-crotylation of 2-methyl-1,3-propane diol directly assembles the triketide stereopolyad spanning C4-C12, significantly enhancing step economy and enabling construction of (+)-zincophorin methyl ester in nearly half the steps previously required.

Publication types

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

MeSH terms

  • Alkylation
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Ionophores / chemical synthesis*
  • Ionophores / chemistry
  • Oxidation-Reduction
  • Polyketides / chemical synthesis
  • Polyketides / chemistry
  • Propylene Glycols / chemical synthesis
  • Propylene Glycols / chemistry
  • Stereoisomerism

Substances

  • Carboxylic Acids
  • Ionophores
  • Polyketides
  • Propylene Glycols
  • zincophorin methyl ester
  • 2-methyl-1,3-propanediol