Document Type
Article
Publication Date
2009
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.
Recommended Citation
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.
DOI:10.1016/j.tetlet.2009.07.074
Copyright
Elsevier
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.
Comments
NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, volume 50, issue 41, in 2009. DOI: 10.1016/j.tetlet.2009.07.074
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