Convenient, scalable synthesis of 2-methyl-3-(3′,3′-carboxymethylpropyl)-1,4-naphthoquinone, the principal vitamin K urinary metabolite

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Abstract

The ultimate metabolite of vitamin K, 2-methyl-3-(3′,3′-carboxymethylpropyl)-1,4-naphthoquinone (1), has been shown to be biologically active and may be used as a measure of vitamin K levels in the body. We report a facile, five-step synthesis of 1 that requires only two isolated intermediates and a single chromatographic purification, and provides the title product in 26% overall yield. The structure of one of the intermediates was confirmed by X-ray crystallography.

Original languageEnglish (US)
Pages (from-to)5850-5851
Number of pages2
JournalTetrahedron Letters
Volume57
Issue number52
DOIs
StatePublished - Jan 1 2016

Keywords

  • Metabolite
  • Naphthoquinone
  • Natural product
  • Total synthesis
  • Vitamin K

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