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AsymmetricGPX-11-21-18.pdf (1.01 MB)
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Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition

preprint
submitted on 21.11.2018 and posted on 23.11.2018 by Michael Smith, Kyle Reichl, Randolph Escobar, Thomas Heavey, David Coker, Scott Schaus, John Porco
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

Funding

GM-118173, GM-078240, CHE-1665367

History

Email Address of Submitting Author

porco@bu.edu

Institution

Boston University

Country

USA

ORCID For Submitting Author

0000-0002-2991-5680

Declaration of Conflict of Interest

No conflict of interest

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