Organic Chemistry

Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition

Abstract

Asymmetric synthesis of the biologically active xanthone dimer griffipavixanthone (GPX) is reported along with its absolute stereochemistry determination. Synthesis of the natural product is accomplished via dimerization of a p-quinone methide (p-QM) using a chiral phosphoric acid (CPA) catalyst to afford a protected precursor in excellent diastereo- and enantioselectivity. Mechanistic studies, including an unbiased computational investigation of chiral ion-pairs using parallel tempering (PT), were performed in order to probe the mode of asymmetric induction

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