Sugar-Pirating as an Enabling Platform for the Synthesis of 4,6-Dideoxyhexoses

Yinan Zhang, Jianjun Zhang, Larissa V. Ponomareva, Zheng Cui, Steven G. Van Lanen, Jon S. Thorson, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

An efficient divergent synthetic strategy that leverages the natural product spectinomycin to access uniquely functionalized monosaccharides is described. Stereoselective 2′- and 3′-reduction of key spectinomycin-derived intermediates enabled facile access to all eight possible 2,3-stereoisomers of 4,6-dideoxyhexoses as well as representative 3,4,6-trideoxysugars and 3,4,6-trideoxy-3-aminohexoses. In addition, the method was applied to the synthesis of two functionalized sugars commonly associated with macrolide antibiotics - the 3-O-alkyl-4,6-dideoxysugar d-chalcose and the 3-N-alkyl-3,4,6-trideoxysugar d-desosamine.

Original languageEnglish
Pages (from-to)9389-9395
Number of pages7
JournalJournal of the American Chemical Society
Volume142
Issue number20
DOIs
StatePublished - May 20 2020

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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