Fat-Derived Aziridines and Their N-Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Sandra Fürmeier et.al.: Fat-Derived Aziridines and Their N-Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Author(s): Sandra Fürmeier, Jürgen O. Metzger

Title: Fat-Derived Aziridines and Their N-Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Date of Upload: 2003

Article: Eur. J. Org. Chem. 2003, 649-659, Department of Chemistry, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany

Keywords: Amino alcohols, Aziridines, Chiral pool, Fatty acids , Nitrogen heterocycles, sustainable development, renewable feedstock, vegetable oil, plant oil

Abstract:

The first successful preparation of the aziridines methyl (9Z,12S,13R)-12,13-epimino-9-octadecenoate (10), derived from vernolic acid, and methyl (9R,10S,12R)-9,10-epimino- 12-hydroxyoctadecanoate (12a) and methyl (9S,10R,12R)- 9,10-epimino-12-hydroxyoctadecanoate (12b), both derived from ricinoleic acid, is reported. These are the first examples of enantiomerically pure fat-derived aziridines. Treatment of the corresponding epoxides with sodium azide and ammonium chloride in ethanol in the presence of water yielded the new azido hydroxy compounds, which could be treated in an improved way with polymer-bound triphenylphosphane to afford the aziridines in good yields. The intermediate azido hydroxy compounds could easily be reduced and so offer access to a variety of interesting a-amino alcohols 17−21. The synthesis of various N-substituted aziridine derivatives 22−29 by treatment of methyl cis-9,10-epiminooctadecanoate (3) with phenyl isocyanate and isothiocyanate, acetyl chloride, alkyl and aryl chloroformates and acrylonitrile is described. Finally, the fat-derived 2,5-dialkyl-substituted pyrrole methyl 9-(5-pentyl-1H-pyrrol-2-yl)nonanoate (9) was obtained. The previously reported bis(aziridine) methyl cis-9,10;cis-12,13-diepiminooctadecanoate, derived from linoleic acid, and tris-(aziridine) methyl cis-9,10;cis-12,13;cis-15,16-triepiminooctadecanoate, derived from linolenic acid,[1] have been subjected to different biological tests and showed cytotoxic and antimicrobial activity as well as remarkable antitumour-promoting and good neuroprotective effects.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/94.pdf (application/pdf)

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