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Synthesis 2007(11): 1663-1670  
DOI: 10.1055/s-2007-966067
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Paramagnetic Fatty Acids and Lipophilic Spin Labels

Mária Baloga, Christoph Abéb, Tamás Kálaia, Heinz-Jürgen Steinhoffb, József Jekőc,d, Kálmán Hideg*a
a Department of Organic and Medicinal Chemistry, University of Pécs, P.O. Box 99, 7602 Pécs, Hungary
b Department of Physics, University of Osnabrück, Barbara Str. 7, 49069 Osnabrück, Germany
c ICN Hungary, P.O. Box 1, 4440 Tiszavasvári, Hungary
d Department of Chemistry, College of Nyíregyháza, Sóstói st. 31/B, 4440 Nyíregyháza, Hungary
Fax: +36(72)536219; e-Mail: kalman.hideg@aok.pte.hu;
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Publication History

Received 28 March 2007
Publication Date:
11 May 2007 (online)

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Abstract

Starting from readily available five-membered cyclic nitrones, paramagnetic analogues of palmitic and hexadec-2E-enoic acids are described with a range of pyrrolidine ring orientations. Herein we report the synthesis of 3,4-disubstituted lipophilic pyrroline nitroxides through a palladium-catalyzed cross-coupling reaction. Lipophilic phosphonium salt and SH-specific labels (methanethiosulfonates and isoselenuronium salts) with allylic and propargylic terminal groups are also described.

Key words

fatty acids - free radicals - Grignard reaction - lipids - palladium­-catalyzed reactions