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 › peer-review

30 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

Keywords

aminosugars
asymmetric syntheses
dihydroxylations
quinic acid
valiolamine

ASJC Scopus subject areas

Catalysis
Chemistry(all)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.199516431

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

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.)",

keywords = "aminosugars, asymmetric syntheses, dihydroxylations, quinic acid, valiolamine",

author = "Shing, {Tony K.M.} and Wan, {Leong H.}",

year = "1995",

month = aug,

day = "18",

doi = "10.1002/anie.199516431",

language = "English",

volume = "34",

pages = "1643--1645",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Enantiospecific Syntheses of Valiolamine and its (1R), (2R), (1R, 2R) Diastereomers from (−)‐Quinic Acid

AU - Shing, Tony K.M.

AU - Wan, Leong H.

PY - 1995/8/18

Y1 - 1995/8/18

N2 - 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.)

AB - 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.)

KW - aminosugars

KW - asymmetric syntheses

KW - dihydroxylations

KW - quinic acid

KW - valiolamine

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 15

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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