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

Tony Kung Ming Shing, Leong H. Wan

Research output: Contribution to journalArticle

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
Externally publishedYes

Fingerprint

Carbasugars
Quinic Acid
Glycoside Hydrolases
Acids
valiolamine

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Enantiospecific Syntheses of Valiolamine and its (1R), (2R), (1R, 2R) Diastereomers from (−)‐Quinic Acid. / Shing, Tony Kung Ming; Wan, Leong H.

In: Angewandte Chemie International Edition in English, Vol. 34, No. 15, 18.08.1995, p. 1643-1645.

Research output: Contribution to journalArticle

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