Title: The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine
Authors: Compernolle, Frans ×
Joly, G
Peeters, Koen
Toppet, Suzanne
Hoornaert, Georges
Kilonda, Amuri #
Issue Date: Jan-1997
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:53 issue:37 pages:12739-12754
Abstract: 1-Amino-1-deoxy-D-glucitol (3) was converted into the 3,4;5,6-di-O-isopropylidene protected ammonium salt 17 which was transformed further into the trans-fused piperidine acetonides 4-8 in six steps and 23-32% overall yield. In the final step, ring closure was effected via cleavage of the N-Boc group of intermediates 27-29 with trimethylsilyl iodide: this enabled internal, face selective 1,4-addition of the free amino group to the (5,6)-alpha,beta-unsaturated carbonyl moiety. Further modification and (or) deprotection of compounds 4-8 afforded the piperidine and indolizidine imino sugars 9-12 and 14-15. (C) 1997 Elsevier Science Ltd.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Chemistry - miscellaneous
× corresponding author
# (joint) last author

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