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

Authors :
Luca McDermott
Clay S. Bennett
Joseph R. Romeo
Source :
Org Lett
Publication Year :
2020
Publisher :
American Chemical Society (ACS), 2020.

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.

Details

ISSN :
15237052 and 15237060
Volume :
22
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....f85295e53afbc6276c05f5035028a2ca
Full Text :
https://doi.org/10.1021/acs.orglett.0c01153