De Novo Asymmetric Synthesis of the Anthrax Tetrasaccharide by a Palladium-Catalyzed Glycosylation Reaction

Authors


  • We thank the NIH (GM63150) and NSF (CHE-0415469) for their generous support of our research program. Funding for a 600-MHz NMR spectrometer by the NSF-EPSCoR (grant 0314742) is also gratefully acknowledged.

Abstract

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Choose your poison: In the de novo asymmetric synthesis of the anthrax tetrasaccharide 1 (25 steps from acetylfuran), the absolute configurations of three L sugars and one D sugar were set by the Noyori reduction of acetylfuran with the S,S and the R,R reagent, respectively. The configuration of the remaining carbohydrate unit was set by highly diastereoselective palladium-catalyzed glycosylation and post-glycosylation transformations.

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