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

Néstor M. Carballeira, Carlos Miranda, Keykavous Parang

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)5699-5700
Number of pages2
JournalTetrahedron Letters
Volume50
Issue number41
DOIs
StatePublished - Oct 14 2009
Externally publishedYes

Fingerprint

Cryptococcus neoformans
Candida
Candida albicans
Fatty Acids
Acids
decanoic acid
compound 17

Keywords

  • Antifungal
  • Candida albicans
  • Decanoic acid
  • Methoxylated fatty acids
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The first total synthesis of (±)-4-methoxydecanoic acid : a novel antifungal fatty acid. / Carballeira, Néstor M.; Miranda, Carlos; Parang, Keykavous.

In: Tetrahedron Letters, Vol. 50, No. 41, 14.10.2009, p. 5699-5700.

Research output: Contribution to journalArticle

Carballeira, Néstor M. ; Miranda, Carlos ; Parang, Keykavous. / The first total synthesis of (±)-4-methoxydecanoic acid : a novel antifungal fatty acid. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 41. pp. 5699-5700.
@article{e584816d6ea544eba8e6f1a12bc681b4,
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.",
keywords = "Antifungal, Candida albicans, Decanoic acid, Methoxylated fatty acids, Synthesis",
author = "Carballeira, {N{\'e}stor M.} and Carlos Miranda and Keykavous Parang",
year = "2009",
month = "10",
day = "14",
doi = "10.1016/j.tetlet.2009.07.074",
language = "English (US)",
volume = "50",
pages = "5699--5700",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "41",

}

TY - JOUR

T1 - The first total synthesis of (±)-4-methoxydecanoic acid

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

UR - http://www.scopus.com/inward/record.url?scp=68949166337&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=68949166337&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.07.074

DO - 10.1016/j.tetlet.2009.07.074

M3 - Article

C2 - 20161109

AN - SCOPUS:68949166337

VL - 50

SP - 5699

EP - 5700

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -