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 ,
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
