The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid.
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.
Carballeira
Néstor M
NM
Department of Chemistry, University of Puerto Rico, Rio Piedras campus, PO BOX 23346, San Juan, Puerto Rico 00931.
Miranda
Carlos
C
Parang
Keykavous
K