(±)-4-甲氧基癸酸的首次全合成：一种新型抗真菌脂肪酸。
The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid.
作者信息
Carballeira Néstor M, Miranda Carlos, Parang Keykavous
机构信息
Department of Chemistry, University of Puerto Rico, Rio Piedras campus, PO BOX 23346, San Juan, Puerto Rico 00931.
出版信息
Tetrahedron Lett. 2009 Oct 14;50(41):5699-5700. doi: 10.1016/j.tetlet.2009.07.074.
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 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.
摘要
从市售的4-戊烯-1-醇出发，通过六步反应合成了此前未知的（±）-4-甲氧基癸酸，总产率为25%。与未取代的正癸酸相比，标题化合物对白色念珠菌ATCC 60193和新型隐球菌ATCC 66031的抗真菌活性高17倍（MIC = 1.5 mM）。我们的结果表明，中链甲氧基化似乎是提高脂肪酸杀真菌毒性的一种可行策略。
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