Asymmetric Synthesis of Homocitric Acid Lactone

J Org Chem. 2016 Nov 18;81(22):11404-11408. doi: 10.1021/acs.joc.6b01997. Epub 2016 Oct 21.

Abstract

A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.

Publication types

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

MeSH terms

  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Spectrum Analysis / methods
  • Stereoisomerism

Substances

  • Lactones
  • homocitrate lactone