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DOI: 10.1055/s-2005-865372
Total Synthesis of the Marine Natural Product rac-Dibromophakellstatin
Contributor(s): Victor Snieckus, Oleg M. DemchukLudwig-Maximilians-Universität, München, Germany
Total Synthesis of the Marine Natural Product rac-Dibromophakellstatin
Angew. Chem. Int. Ed. 2005, 44: 2295-2298
Publication History
Publication Date:
20 July 2005 (online)
Key words
dibromopha-kellstatin - total synthesis - tetracyclic - imidazolinones - alkaloids
Significance
A synthesis of rac-dibromophakellstatin in five steps with unknown overall yield is reported. The crucial synthetic step is the unusual D-ring formation, which involves the reaction of the electron-rich enamine (B-ring) with a nitrogen electrophile. An NMR study and X-ray crystallographic analysis are reported.
Comment
Pyrrole-imidazole alkaloids constitute a family of over 100 natural products with interesting pharmacological activities, including cytotoxicity and immunosuppressive activity. The current synthesis may be compared to previous multisteps routes (up to 15 steps for enantiomerically pure compounds) (L. H. Foley, G. Büchi J. Am. Chem. Soc. 1982, 104, 1776-1777; K. J. Wiese, K. Yakushijin, D. A. Horne Tetrahedron Lett. 2002, 43, 5135-5136; K. G. Poullennec, D. Romo J. Am. Chem. Soc. 2003, 125, 6344-6345). The unusual ring D construction step may find application in other systems for imidazolidinone annelations.