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Synlett 1996; 1996(12): 1181-1183
DOI: 10.1055/s-1996-5704
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Concise Synthesis of Deacetylanisomycin and 2-Substituted Analogues from N,2-O-Dibenzyl-L-threose Imine1

Ulrich Veith, Oliver Schwardt, Volker Jäger*
  • *Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax +711/685-4321, e-mail ioc@po.uni-stuttgart.de
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Publication Date:
31 December 2000 (online)

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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.

Threose imine - diastereoselective 1,2-addition - δ-amino alcohol cyclization - dihydroxypyrrolidine - anisomycin analogues