Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade
Kyle D Reichl1, Michael J Smith1, Min K Song2
1Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
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.
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