Graduate Thesis Or Dissertation
 

Part I: Synthetic Studies Toward Mandelalide A and Madeirolide A; Part II: Synthesis of Mandelalide/Madeirolide Hybrid Structures

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  • Mandelalide A has attracted considerable interest from the synthetic community due to its intriguing structure and important cytotoxic activity. Madeirolide A, a structurally related macrolide, shows promising antifungal activity but no appreciable anticancer activity. This dissertation describes synthetic studies toward mandelalide A, madeirolide A and their hybrid structures. Part I of this dissertation introduces the background of mandelalide A and madeirolide A as well as the synthesis of the C1-C12 southern subunit of madeirolide A. A key feature of the synthesis involves Ag-Catalyzed Cyclization (AgCC) of β-hydroxypropargylic benzoate to construct the tetrasubstituted pyran ring. The substrates and conditions of Ag-Catalyzed Cyclization (AgCC) reaction to access tetrasubstituted pyran was explored. Part I also details the synthetic studies toward the synthesis of the northern fragment of mandelalide A. Part II of this dissertation details the synthetic studies toward mandelalide/madeirolide hybrid macrolide structures. During the synthesis, a practical and high yielding approach to access tetrasubstituted cis-THP ring via TFA-mediated Prins cyclization was developed. A second-generation synthesis of the northern fragment of mandelalide A is also discussed. The diastereoselectivity of Sharpless dihydroxylation was improved. The macrocyclic ring was constructed via Wittig reaction followed by Shiina macrolactonization. The investigation of glycosylation conditions is also discussed.
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  • Ongoing Research
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  • 2019-06-13 to 2021-07-13
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