Total synthesis of (-)-dysibetaine via a nitrenium ion cyclization-dienone cleavage strategy |
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Authors: | Wardrop Duncan J Burge Matthew S |
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Institution: | Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60201-7061, USA. wardropd@uic.edu |
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Abstract: | 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. |
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