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Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

TitleConcise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy
Publication TypeJournal Article
Year of Publication2014
AuthorsZoidl, M, Mueller, B, Torvisco, A, Tysoe, C, Benazza, M, Siriwardena, A, Withers, SG, Wrodnigg, TM
JournalBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume24
Pagination2777-2780
Date PublishedJUN 15
ISSN0960-894X
Abstract

A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.

DOI10.1016/j.bmcl.2014.03.069