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Enantioselective Synthesis of the Core of Banyaside, Suomilide, and Spumigin HKVV

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  • This work was supported by a grant from the Swiss National Science Foundation. C.S.S. thanks the Roche Research Foundation for a predoctoral fellowship. We are grateful to Dr. W. Bernd Schweizer for the X-ray crystallographic analysis of compounds 7 a and 18.

Abstract

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Concise: The first synthesis of the unique azabicyclononane core found in the aeruginosin class of serine protease inhibitors is described. The route is characterized by its efficiency (eight steps) and sets the stage for subsequent introduction of the glycosyl and peptidyl side chains that differentiate the members of the aeruginosin family of natural products.

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