Kim, Gina Jane2018-03-052017https://hdl.handle.net/2144/27370Tetrahydroxanthones 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.en-USChemistryTetrahydroxanthoneThesis/Dissertation2018-02-14