Total synthesis of (−)-dysibetaine via a nitrenium ion cyclization–dienone cleavage strategy

Literature Information

Publication Date 2004-04-27
DOI 10.1039/B403081H
Impact Factor 6.222
Authors

Duncan J. Wardrop, Matthew S. Burge


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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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