Synthesis 2017; 49(03): 615-636
DOI: 10.1055/s-0036-1588314
paper
© Georg Thieme Verlag Stuttgart · New York

Modular Regiospecific Synthesis of Nitrated Fatty Acids

Katharina J. Hock
a  Institute 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
a  Institute 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
a  Institute 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
a  Institute 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
b  Institute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany
,
Isabelle V. Maucher
b  Institute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany
,
Benjamin Kühn
b  Institute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany
,
Jasmin Fettel
b  Institute of Pharmaceutical Chemistry/ZAFES, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438, Frankfurt/Main, Germany
,
Thorsten J. Maier
c  Department of Biomedicine, Aarhus University, Bartholins Allé 6, 8000 Aarhus C, Denmark
,
Georg Manolikakes*
a  Institute 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
› Author Affiliations
Further Information

Publication History

Received: 03 August 2016

Accepted after revision: 25 August 2016

Publication Date:
21 September 2016 (online)

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.

Supporting Information

 
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