The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid

Néstor M. Carballeira, Carlos Miranda, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


The hitherto unknown (±)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated 17-fold higher antifungal activity (MIC = 1.5 mM) against Candida albicans ATCC 60193 and Cryptococcus neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids.

Original languageEnglish (US)
Pages (from-to)5699-5700
Number of pages2
JournalTetrahedron Letters
Issue number41
StatePublished - Oct 14 2009
Externally publishedYes


  • Antifungal
  • Candida albicans
  • Decanoic acid
  • Methoxylated fatty acids
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery


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