2. Academic Validation
  3. Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide

Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide

  • Org Lett. 2020 May 1;22(9):3649-3654. doi: 10.1021/acs.orglett.0c01153.
Joseph R Romeo 1,  Luca McDermott 1,  Clay S Bennett 1
Affiliations

Affiliation

  • 1 Department of Chemistry, Tufts University, Medford, Massachusetts 02155, United States.
PMID: 32281384 DOI: 10.1021/acs.orglett.0c01153
Abstract

The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the α-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.

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