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osu1306336570.pdf (7.72 MB)
ETD Abstract Container
Abstract Header
Synthetic Studies Toward Marine Natural Product Okadaic Acid and Its Analogs
Author Info
Fang, Chao
Permalink:
http://rave.ohiolink.edu/etdc/view?acc_num=osu1306336570
Abstract Details
Year and Degree
2011, Doctor of Philosophy, Ohio State University, Chemistry.
Abstract
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.
Committee
Craig Forsyth (Advisor)
James Stambuli (Committee Member)
Dehua Pei (Committee Member)
Jack Rall (Committee Member)
Pages
198 p.
Subject Headings
Chemistry
Keywords
okadaic acid
;
spiroketal synthesis
;
gold catalysis
;
belizeanic acid
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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)
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Document number:
osu1306336570
Download Count:
678
Copyright Info
© 2011, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.