Total synthesis of (-)-dysibetaine via a nitrenium ion cyclization-dienone cleavage strategy.
The diastereoselective total synthesis of the marine natural product (-)-dysibetaine is reported. The key steps in this venture are i) a diastereoselective nitrenium ion spirocyclization, which serves to generate the pyrrolidinone ring and quaternary stereocenter of the target, and ii) use of the 2-methoxycyclohexa-2,5-dienone ring formed during cyclization as a masked 2-amino-1,3-dicarbonyl synthon.
Wardrop
Duncan J
DJ
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60201-7061, USA. wardropd@uic.edu
Burge
Matthew S
MS
D003500:Cyclization; D011760:Pyrrolidinones / Q000138:chemical synthesis*
D011760:Pyrrolidinones; C431075:dysibetaine