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The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid
Authors:  stor M. Carballeira,Carlos Miranda
Affiliation:a Department of Chemistry, University of Puerto Rico, Rio Piedras campus, P.O. Box 23346, San Juan, PR 00931, USA
b Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI, USA
Abstract: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.
Keywords:Antifungal   Candida albicans   Decanoic acid   Methoxylated fatty acids   Synthesis
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