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    Studies toward the syntheses of tetrahydroswertianolin and puniceaside B

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    Date Issued
    2017
    Author(s)
    Kim, Gina Jane
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    https://hdl.handle.net/2144/27370
    Abstract
    Tetrahydroxanthones are a family of natural products with chemically interesting functional groups and a diverse array of reported biological activities. The dissertation research described herein has been focused on the synthesis of tetrahydroswertianolin, a glycosylated tetrahydroxanthone, and puniceaside B, a heterodimeric, glycosylated tetrahydroxanthone. To the best of our knowledge, there have been no published reports on the total synthesis of either natural product. We have targeted tetrahydroswertianolin and puniceaside B in hopes of developing a divergent method to easily access a variety of tetrahydroxanthone cores for natural product and analogue synthesis. Our efforts to develop a cascade reaction toward the tetrahydroxanthone core and the stepwise route that we simultaneously pursued will be presented. A scalable synthetic route to the tetrahydroxanthone core of tetrahydroswertianolin and the aromatic xanthone core of puniceaside B was accomplished. An asymmetric route to the tetrahydroxanthone precursor was also developed.
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