Enantiospecific Syntheses of Valiolamine and its (1R), (2R), (1R, 2R) Diastereomers from (−)‐Quinic Acid

Tony K.M. Shing, Leong H. Wan

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29 Citations (Scopus)

Abstract

Applicable also for other pseudosugars, the simple reaction sequence for the preparation of α‐D‐glucosidase inhibitors valiolamine (1) and its three diastereoisomers starts with 1,3,4,5‐tetrahydroxycyclohexanecarboxylic acid (quinic acid). Glycosidase inhibitors like 1 are used as chemotherapeutics, for example, against HIV. (Figure Presented.)

Original languageEnglish
Pages (from-to)1643-1645
Number of pages3
JournalAngewandte Chemie International Edition in English
Volume34
Issue number15
DOIs
Publication statusPublished - 1995 Aug 18

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Keywords

  • aminosugars
  • asymmetric syntheses
  • dihydroxylations
  • quinic acid
  • valiolamine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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