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Keywords:

  • antibiotics;
  • atropisomerism;
  • natural product synthesis;
  • samarium;
  • total synthesis

Abstract

Thumbnail image of graphical abstract

Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular SNAr reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI2-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.