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

Tony K.M. Shing; Leong H. Wan

doi:10.1002/anie.199516431

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

Tony K.M. Shing, Leong H. Wan

Department of Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1643-1645
Number of pages	3
Journal	Angewandte Chemie International Edition in English
Volume	34
Issue number	15
DOIs	https://doi.org/10.1002/anie.199516431
Publication status	Published - 1995 Aug 18

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Keywords

aminosugars
asymmetric syntheses
dihydroxylations
quinic acid
valiolamine

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Cite this

Shing, T. K. M., & Wan, L. H. (1995). Enantiospecific Syntheses of Valiolamine and its (1R), (2R), (1R, 2R) Diastereomers from (−)‐Quinic Acid. Angewandte Chemie International Edition in English, 34(15), 1643-1645. https://doi.org/10.1002/anie.199516431

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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.)",

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Access to Document

10.1002/anie.199516431