Enantiospecific synthesis of pseudoacarviosin as a potential antidiabetic agent

Tony K.M. Shing, Hau M. Cheng, Wai F. Wong, Connie S.K. Kwong, Jianmei Li, Clara B.S. Lau, Sing Leung Po, Christopher H.K. Cheng

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

(Chemical Equation Presented) A pseudo-1,4′-N-linked disaccharide, pseudoacarviosin 5, was constructed via a key palladium-catalyzed coupling reaction of pseudoglycosyl chloride 8 (prepared from d-glucose via a novel direct intramolecular aldol addition in 12 steps) and pseudo-4-amino-4,6- dideoxy-α-d-glucose 9 (prepared from l-arabinose via an unusual trans-fused isoxazolidine-selective intramolecular nitrone-alkene cycloaddition in 11 steps). Pseudoacarviosin 5 has been shown to be a potent inhibitor of α-glucosidases, particularly the intestinal mucosal enzymes sucrase and glucoamylase of relevance to blood glucose control.

Original languageEnglish
Pages (from-to)3145-3148
Number of pages4
JournalOrganic Letters
Volume10
Issue number14
DOIs
Publication statusPublished - 2008 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Shing, T. K. M., Cheng, H. M., Wong, W. F., Kwong, C. S. K., Li, J., Lau, C. B. S., Po, S. L., & Cheng, C. H. K. (2008). Enantiospecific synthesis of pseudoacarviosin as a potential antidiabetic agent. Organic Letters, 10(14), 3145-3148. https://doi.org/10.1021/ol8010503