Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 1, Pages 148-153Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b12520
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Funding
- National Institutes of Health (NIH) [R35 GM-118173]
- Boston University (BU)
- NIH [R24 GM-111625, R01 GM-078240]
- American Cancer Society [PF-16-235-01-CDD]
- National Science Foundation (NSF) [CHE-0619339, CHE-0443618]
- NSF [CHE-1665367]
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Asymmetric synthesis of the biologically active xanthone dimer griffipavixanthone is reported along with its absolute stereochemistry determination. Synthesis of the natural product is accomplished via dimerization of a p-quinone methide using a chiral phosphoric acid 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, were performed in order to probe the mode of asymmetric induction.
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