Studies directed towards the total synthesis of (+)-peloruside A

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Engers, Darren William

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Peloruside A, isolated from marine sponge Mycale hentscheli, has shown potent cytotoxicity toward P388 murine leukemia cells (10 ng/mL, 18 nM), and functions like Taxol® by inducing apoptosis in the G2-M phase of the cell cycle through microtubulestabilization. To date, there have been two total synthesis of peloruside A. The goal of our research was to have the most efficient and practical synthesis of peloruside A. In this study, the application of a variety of aldol methodologies towards the convergent synthesis of peloruside A will be discussed. In our initial approach, the key synthetic strategy for peloruside A is the Mukaiyama aldol reaction between a glucosederived aldehyde and an α-benzyloxymethyl ketone. Alternatively, a similar segment of peloruside A can be constructed with a complex methyl ketone using a Walsh multicomponent coupling reaction and a Carreira enantioselective dienolate addition. The study is concluded with a concise synthesis of an advanced intermediate of peloruside A.




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