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Synthetic Studies Toward Marine Natural Product Okadaic Acid and Its Analogs

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2011, Doctor of Philosophy, Ohio State University, Chemistry.
Okadaic acid is a potent and selective inhibitor of protein serine/threonine phosphatase 1 and 2A (PP1 and PP2A), and has been widely used as a laboratory tool for identifying and studying many essential cellular processes associated with the inhibition of protein phosphatases. In order to understand the structural basis of its activity toward protein phosphatases, an efficient and flexible total synthesis of okadaic acid was developed in the Forsyth group in 1997. This dissertation describes recent efforts to improve the synthetic approach toward okadaic acid and its analogs. The first part of the work includes an efficient synthesis of C15-C38 fragment of okadaic acid and 29-desmethylokadaic acid, highlighted by the application of gold-catalyzed regiocontrolled spiroketalization to synthesize the central and tail spiroketal moieties. This method provides a reliable alternative to the conventionally used acid-catalyzed dehydrative cyclization approach. The second part of the dissertation describes a total synthesis of belizeanic acid, a structurally related analog of okadaic acid. The synthesis is based on the methods developed in our synthesis of okadaic acid, and will provide valuable materials for biological tests.
Craig Forsyth (Advisor)
James Stambuli (Committee Member)
Dehua Pei (Committee Member)
Jack Rall (Committee Member)
198 p.

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Citations

  • Fang, C. (2011). Synthetic Studies Toward Marine Natural Product Okadaic Acid and Its Analogs [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1306336570

    APA Style (7th edition)

  • Fang, Chao. Synthetic Studies Toward Marine Natural Product Okadaic Acid and Its Analogs. 2011. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1306336570.

    MLA Style (8th edition)

  • Fang, Chao. "Synthetic Studies Toward Marine Natural Product Okadaic Acid and Its Analogs." Doctoral dissertation, Ohio State University, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=osu1306336570

    Chicago Manual of Style (17th edition)