Decomposition of oroidin in DMSO/TFA |
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| Authors: | Thomas Lindel Gregor Breckle Christian Volk Matthias Köck |
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| Institution: | a Ludwig-Maximilians-Universität, Department of Chemistry and Biochemistry, D-81377 Munich, Germany
b Alfred-Wegener-Institut für Polar- und Meeresforschung in der Helmholtz-Gemeinschaft, D-27570 Bremerhaven, Germany |
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| Abstract: | Oxidative cyclization of the pyrrole-imidazole alkaloids oroidin and sventrin in DMSO/TFA (1:1) yields oxazolines via nucleophilic attack of the carbonyl oxygen at the alkenyl double bond. Oxidation takes place in the benzylic position of the imidazole ring. On prolonged reaction times, the oxazoline ring is hydrolyzed yielding the corresponding ester of pyrrole-2-carboxylic acid containing a free amino group. Overall, the double bond of oroidin is dioxygenated. |
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| Keywords: | Aminoimidazoles Marine natural products Medicinal chemistry Oxazolines Pyrrole-imidazole alkaloids |
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