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

✍ Scribed by Néstor M. Carballeira; Carlos Miranda; Keykavous Parang

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
181 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 seventeen 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.

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