Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade

  • J Am Chem Soc. 2017 Oct 11;139(40):14053-14056. doi: 10.1021/jacs.7b09265.
Kyle D Reichl  1 ,  Michael J Smith  1 ,  Min K Song  2 ,  Richard P Johnson  2 ,  John A Porco Jr  1
Affiliations
  • 1. Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
  • 2. Department of Chemistry and Materials Science Program, University of New Hampshire , Durham, New Hampshire 03824, United States.
PMID: 28942643 DOI: 10.1021/jacs.7b09265
Abstract

We report the concise, biomimetic total synthesis of the dimeric, Diels-Alder natural product griffipavixanthone from a readily accessible prenylated xanthone monomer. The key step utilizes a novel intermolecular [4+2] cycloaddition-cyclization cascade between a vinyl p-quinone methide and an in situ generated isomeric diene promoted by either Lewis or Brønsted acids. Experimental and computational studies of the reaction pathway suggest that a stepwise, cationic Diels-Alder cycloaddition is operative.

Products