Title of article
Decomposition of oroidin in DMSO/TFA
Author/Authors
Lindel، نويسنده , , Thomas and Breckle، نويسنده , , Gregor and Hochgürtel، نويسنده , , Matthias and Volk، نويسنده , , Christian and Grube، نويسنده , , Achim and Kِck، نويسنده , , Matthias، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2004
Pages
4
From page
8149
To page
8152
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.
Keywords
Oxazolines , marine natural products , Medicinal chemistry , pyrrole–imidazole alkaloids , Aminoimidazoles
Journal title
Tetrahedron Letters
Serial Year
2004
Journal title
Tetrahedron Letters
Record number
1843691
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