Reichl, Kyle D.Smith, Michael J.Song, Min K.Johnson, Richard P.Porco, John A.2018-11-062018-11-062017-10-11Kyle D Reichl, Michael J Smith, Min K Song, Richard P Johnson, John A Porco. 2017. "Biomimetic Total Synthesis of (+/-)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade." Journal Of The American Chemical Society, Volume 139, Issue 40, pp. 14053 - 14056 (4). https://doi.org/10.1021/jacs.7b092650002-7863https://hdl.handle.net/2144/31952Published in final edited form as: J Am Chem Soc. 2017. October 11; 139(40): 14053–14056. doi:10.1021/jacs.7b09265.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.p. 14053 - 14056Science & technologyPhysical sciencesChemistryPara-quinone methidesDiels-Alder reactionsGarcinia-oblongifoliaAllyl cationsIn-vitroXanthonesGriffipavixanthoneMechanismBarkXanthochymusBiological productsBiomimeticsCrystallography, X-rayCyclizationCycloaddition reactionModels, molecularStereoisomerismXanthonesChemical sciencesArticle10.1021/jacs.7b0926528942643