Modular Regiospecific Synthesis of Nitrated Fatty Acids

Katharina J. Hock; Jennifer Grimmer; Dominik Göbel; George Gichogo T. Gasaya; Jessica Roos; Isabelle V. Maucher; Benjamin Kühn; Jasmin Fettel; Thorsten J. Maier; Georg Manolikakes

doi:10.1055/s-0036-1588314

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(03): 615-636
DOI: 10.1055/s-0036-1588314

paper

Modular Regiospecific Synthesis of Nitrated Fatty Acids

Katharina J. Hock

^aInstitute of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt/Main, Germany eMail: g.manolikakes@chemie.uni-frankfurt.de

,

Jennifer Grimmer

^aInstitute of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt/Main, Germany eMail: g.manolikakes@chemie.uni-frankfurt.de

,

Dominik Göbel

^aInstitute of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt/Main, Germany eMail: g.manolikakes@chemie.uni-frankfurt.de

,

George Gichogo T. Gasaya

^aInstitute of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt/Main, Germany eMail: g.manolikakes@chemie.uni-frankfurt.de

,

Jessica Roos

^bInstitute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany

,

Isabelle V. Maucher

^bInstitute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany

,

Benjamin Kühn

^bInstitute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany

,

Jasmin Fettel

^bInstitute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany

,

Thorsten J. Maier

^cDepartment of Biomedicine, Aarhus University, Bartholins Allé 6, 8000 Aarhus C, Denmark

,

Georg Manolikakes*

^aInstitute of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt/Main, Germany eMail: g.manolikakes@chemie.uni-frankfurt.de

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Abstract

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^‡ Both authors contributed equally to this study.

Abstract

Endogenous nitrated fatty acids are an important class of signaling molecules. Herein a modular route for the efficient and regiospecific preparation of nitrooleic acids as well as various analogues is described. The approach is based on a simple set of alkyl halides as common building blocks and a Henry reaction/Burgess dehydration sequence for the formation of the key nitroalkene moiety.

Key words

medicinal chemistry - nitroaldol reaction - nitrated fatty acid - Burgess reagent - nitroolefin

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Referenzen

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