First stereoselective total synthesis of FD-594 aglycon

Angew Chem Int Ed Engl. 2009;48(19):3462-5. doi: 10.1002/anie.200806338.

Abstract

Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular S(N)Ar reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI(2)-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibiotics, Antineoplastic / chemical synthesis*
  • Antibiotics, Antineoplastic / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Stereoisomerism
  • Streptomyces / chemistry
  • Streptomyces / metabolism
  • Xanthenes / chemical synthesis*
  • Xanthenes / chemistry

Substances

  • Antibiotics, Antineoplastic
  • FD 594, antibiotic
  • Lactones
  • Pyrans
  • Xanthenes