Diels−Alder Reactions of Oroidin and Model Compounds

• DOI: 10.1021/ol0526219
• Publication Date: 2006-02-23T05:55:26Z
• Authors: Christoph Pöverlein; Gregor Breckle; Thomas Lindel
• Keywords: Models, Molecular; Alkaloids; Molecular Structure; Cyclization; Temperature; Animals; Pyrroles; 01 natural sciences; Porifera; 3. Good health; 0104 chemical sciences

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.