Concise synthesis of deacetylanisomycin and 2-substituted analogues from N,2-O-dibenzyl-1-threose imine

Anisomycin derivatives like deacetylanisomycin 8k and 2-substituted analogues have been prepared using a highly threo-selective addition of organolithium and Grignard compounds to N,2-O-dibenzyl-L-threose imine acetonide 4 and subsequent cyclization as key steps.

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Bibliographic Details
Published inSynlett no. 12; pp. 1181 - 1184
Main Authors Veith, U, Schwardt, O, Jager
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.1996
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIFUNGAL AGENT
ANTIBIOTICS
(-)-ANISOMYCIN
ANISOMYCIN
GLYCOSIDASE INHIBITORS
dihydroxypyrrolidine
delta-amino alcohol cyclization
STEREOSELECTIVE SYNTHESIS
ENANTIOMER
threose imine
ENANTIOSELECTIVE TOTAL SYNTHESIS
diastereoselective 1,2-addition
anisomycin analogues
EFFICIENT
CYCLIZATION
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Summary:Anisomycin derivatives like deacetylanisomycin 8k and 2-substituted analogues have been prepared using a highly threo-selective addition of organolithium and Grignard compounds to N,2-O-dibenzyl-L-threose imine acetonide 4 and subsequent cyclization as key steps.
ISSN:0936-5214