Total Synthesis of Mangrolide A




Yu, Xueliang

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The discovery of antibiotics in the 1930s played a critical role in human health by treatment of patients with kinds of infections. During the 'golden era' of antibiotic research, various antibiotics were discovered. The emergence of multi-drug-resistant bacteria has jeopardized the human health. The total synthesis of the natural products plays a crucial part in modern organic chemistry. Mangrolide A was isolated from a rare marine actinomycete strain Actinoalloteichus spitensis by MacMillan and co-workers in 2013. The first part of this thesis will extensively review the synthesis of tiacumicin B which is structurally similar to mangrolide A and also an FDA approved antibiotic. Due to the presence of aminoglycoside in mangrolide A, the glycosylation chemistry of related sugars will also be reviewed. The second part of this thesis is about the total synthesis of mangrolide A and analogs. Base on the studies of MacMillan's group, mangrolide A could not generate the aglycone under acidic conditions. In another path, the desired product mangrolide A methyl ether was achieved along with several rearrangement products. Due to the lack of free hydroxy group at C11, the absolute stereochemistry could not be determined by the standard method (e.g., Mosher's analysis). Synthesis of the desired mangrolide A methyl ether can confirm the stereochemistry and simplify the work of total synthesis of mangrolide A. A rare 2,3-epoxide glycoside was used to install the disaccharide of mangrolide A.

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