Diels-Alder reactions of oroidin and model compounds.
It is shown that the marine key metabolite oroidin undergoes Diels-Alder reactions with electron-poor dienophiles. However, on heating of oroidin in the absence of any reaction partner, cyclization to the natural product cyclooroidin takes place. This is the first direct conversion of oroidin to another pyrrole-imidazole alkaloid.
Pöverlein
Christoph
C
Department of Chemistry and Biochemistry, Ludwig Maximilian University, Butenandtstrasse 5-13, D-81377 Munich, Germany.
Breckle
Gregor
G
Lindel
Thomas
T
D000470:Alkaloids / Q000737:chemistry*; D000818:Animals; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D013696:Temperature
D000470:Alkaloids; D011758:Pyrroles; C077209:oroidin