Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 2
230
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Alternative, High‐Yield Synthesis of (E)‐4‐Oxonon‐2‐enoic Acid from 2‐Methoxyfuran

, &
Pages 212-216 | Received 08 Jun 2007, Published online: 18 Jan 2008

References

  • Pfefferle , C. , Kempter , C. , Metzger , J. W. and Feidler . 1996 . Biosynthetic capacities of actinomycetes. no. 8: (E)‐4‐oxonon‐2‐enoic acid, an antibiotically active fatty acid produced by Streptomyces olivaceus Tue 4018 . J. Antibiotics , 49 : 826 – 828 .
  • Doorn , J. A. , Hurley , T. D. and Petersen , D. R. 2006 . Inhibition of human mitochondrial aldehyde dehydrogenase by 4‐hydroxynon‐2‐enal and 4‐oxonon‐2‐enal . Chem. Res. Toxicology , 19 : 102 – 110 .
  • Obrecht , D. and Weiss , B. 1989 . New method for the preparation of (E)‐3‐acylprop‐2‐enoic acids . Helvetica Chim. Acta , 72 : 117 – 122 .
  • Annangudi , S. P. , Sun , M. and Salomon , R. G. 2005 . An efficient synthesis of 4‐oxoalkenoic acids from 2‐alkylfurans . Synlett. , : 1468 – 1470 .
  • Breusch , F. L. and Keskin , H. 1948 . Synthesis of hydroxy and keto fatty acids . Arch. Biochem. , 18 : 305 – 318 .
  • Ernest , I. and Jelinkova , H. 1959 . Decomposition of diazoketones with cupric oxide, VIII: preparation of aliphatic β‐acrylacrylic acids . Collect. Czech. Chem. Commun. , 24 : 3341 – 3347 .
  • Kawashima , M. and Fujisawa , T. 1984 . A convenient method for the synthesis of 4‐chloro‐3‐alkenoic acids: a new useful synthetic block for 4‐oxoalkanoic and 4‐oxo‐2‐alkenoic acids . Chem. Lett. , : 1851 – 1854 .
  • Zav'yalov , S. I. , Zavozin , A. G. and Kravchenko , N. E. 1991 . Meldrum's acid as a reagent for synthesis of unsaturated γ‐lactones and β‐acylacrylic acids . Izvestiya Akad. Nauk SSSR, Seriya Khimicheskaya , : 1212 – 1214 .
  • Ballini , R. and Bosica , G. 1998 . Synthesis of (E)‐4‐oxonon‐2‐enoic acid, a natural antibiotic produced by Streptomyces olivaceus . J. Nat. Prod. , 61 : 673 – 674 .
  • Shet , J. , Desai , V. and Tilve , S. 2004 . Domino primary alcohol oxidation‐Wittig reaction: Total synthesis of ABT‐418 and (E)‐4‐oxonon‐2‐enoic acid . Synthesis , : 1859 – 1863 .
  • Margaros , L. , Montagnon , T. , Tofi , M. , Pavlakos , E. and Vassilikogiannakis , G. 2006 . The power of singlet oxygen chemistry in biomimetic syntheses . Tetrahedron , 62 : 5308 – 5317 .
  • Onitsuka , S. , Nishino , H. and Kurosawa , K. 2001 . Photooxygenation of 3‐acetyl‐5‐aryl‐2‐methylfurans via endoperoxide intermediate and the following reactions . Tetrahedron , 57 : 6003 – 6009 .
  • Altundas , R. and Balci , M. 1993 . Photooxygenation of an enol ether: Synthesis of exo‐ and endo‐3,4‐dioxa‐2,5‐dimethoxy‐7,8‐benzo[4.2.2.02,5]deca‐7,9‐diene and its chemical transformations . Tetrahedron , 49 : 6521 – 6526 .
  • Wyman , G. M. 1955 . The cis‐trans isomerization of conjugated compounds . Chem. Rev , 55 : 625 – 657 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.