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Enantiospecific Syntheses of Valiolamine and its (1 R ), (2 R ), (1 R , 2 R ) Diastereomers from (−)‐Quinic Acid
Author(s) -
Shing Tony K. M.,
Wan Leong H.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199516431
Subject(s) - quinic acid , diastereomer , stereochemistry , chemistry , sequence (biology) , human immunodeficiency virus (hiv) , organic chemistry , biochemistry , biology , virology
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.