Studies towards the syntheses of the citreamicins
Embargo Date
2024-02-23
OA Version
Citation
Abstract
Polycyclic xanthone natural products (PXNPs) are a family of polyketides which are characterized by their highly oxygenated, angular hexacyclic frameworks and a diverse range of biological activities. The dissertation research described herein has been focused on the syntheses of the citreamicins, a subset of polycyclic xanthone natural products with a unique five-membered hemiaminal moiety. To the best of our knowledge, there have been no published reports on the total synthesis of any member of the citreamicins subclass. We have targeted the citreamicins in hopes of developing a concise method to easily access the citreamicin family and other related PXNPs.
In the effort to synthesize the congener citreamicin η, two different synthetic routes that we simultaneously pursued will be presented. In the first route, a convergent regioselective arylation of xanthone quinone monoketals was developed. In the second route, a one-pot, regioselective Diels-Alder/oxidation reaction was accomplished. Finally, a novel acyl radical cyclization was employed to construct the pentacyclic core of citreamicin η under mild reaction conditions.