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.
Carballeira, Néstor M., Carlos Miranda, and Keykavous Parang. "The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid." Tetrahedron letters 50, no. 41 (2009): 5699-5700.
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