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Keywords:

  • antitumor antibiotics;
  • aromatic polyketides;
  • axial chirality;
  • pinacol coupling;
  • total synthesis
Thumbnail image of graphical abstract

Solution to a difficult problem: The selective glycosylation of one hydroxy group of the pseudo-C2-symmetric trans diol of benanomicin–pradimicin antibiotics presents a significant synthetic challenge. Sequential asymmetric cleavage of a biaryl lactone and pinacol cyclization (see scheme) provide access to these compounds as well as the naphthoxanthene antibiotic FD-594. The product diol emerges differentially protected from the pinacol coupling.