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Keywords:

  • allylsilanes;
  • macrolide;
  • exo-methylene pyrans;
  • sp2-sp3 coupling;
  • Stille reaction;
  • zampanolide

Abstract

Studies towards the synthesis of the macrocyclic core of (−)-zampanolide are reported. The synthetic approach features a one-pot reduction/vinylogous aldol reaction for construction of the C-15–C-20 fragment, an intramolecular silyl-modified Sakurai (ISMS) reaction for construction of the 2,6-cis-disubstituted exo-methylene pyran subunit, and use of an sp2-sp3 Stille reaction for macrocyclization.