Chirality Relay To Access Oxygenated Angular Aromatic Polyketides


  • We thank the National Institutes of Health for support.


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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.