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

Néstor M. Carballeira; Carlos Miranda; Keykavous Parang

doi:10.1016/j.tetlet.2009.07.074

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

Néstor M. Carballeira, Carlos Miranda, Keykavous Parang

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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.

Original language	English (US)
Pages (from-to)	5699-5700
Number of pages	2
Journal	Tetrahedron Letters
Volume	50
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.074
State	Published - Oct 14 2009
Externally published	Yes

Keywords

Antifungal
Candida albicans
Decanoic acid
Methoxylated fatty acids
Synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tetlet.2009.07.074

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

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.",

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T2 - a novel antifungal fatty acid

AU - Carballeira, Néstor M.

AU - Miranda, Carlos

AU - Parang, Keykavous

PY - 2009/10/14

Y1 - 2009/10/14

N2 - 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.

AB - 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.

KW - Antifungal

KW - Candida albicans

KW - Decanoic acid

KW - Methoxylated fatty acids

KW - Synthesis

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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