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Keywords:

  • antitumor agents;
  • asymmetric allylation;
  • cytotoxicity;
  • macrolides;
  • olefin metathesis

Abstract

Total, stereoselective syntheses of the naturally occurring, cytotoxic macrolides aspergillide A and B are described. Olefin metatheses and asymmetric allylations were key steps in the synthetic sequences. Cytotoxicity assays against several tumor cell lines have been performed for the two aspergillides and some of the intermediates or side products of the synthetic sequence. One of these intermediates has been found markedly active against the human leukemia cancer cell line HL-60, with an IC50 value comparable with that of the clinical drug fludarabine.