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Efforts towards the Total Synthesis of Azaspiracid-3

Zhang, Zhigao
http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671

Abstract Details

2013, Doctor of Philosophy, Ohio State University, Chemistry.
Azaspiracid, a structurally complex marine toxin isolated from the mussel Mytilus edulis in Killary Harbor, Ireland, represents a new class of marine metabolites unrelated to any previous known agent of diarrhetic shellfish posioning. As such, the natural product has spurred considerable interest among organic community. The thesis details the study towards the total synthesis of azaspiracid-3. The C1-C21 domain and C22-C40 domain have been synthesized, which aims to assemble the molecule through Yamaguchi esterification. The ABCD domain involved an efficient NHK coupling reaction between C1-C12 segment and C13-C22 segment. The trioxadispiroketal skeleton was constructed under the influence of acid catalysis. The EFGHI domain highlighted a chelate controlled Mukaiyama aldol reaction to produce C22-C40 linear precursor, and a DIHMA process to assemble the bridged ketal. With the recognition of bridged ketal and spiroaminal functionality in the FGHI domain, the gold-catalysis to achieve these moieties has been proposed. A novel gold-catalyzed spiroaminal formation has been systemically developed. The gold-catalyzed ketallization was then successfully implemented to construct the bridged ketal, while an inevitable elimination could not deliver the desired spiroaminal under gold conditions. A NHK reaction to couple the C1-C21 and C22-C40 domains has also been proposed. The revised C22-C40 domain was achieved with a similar synthetic route.
Craig Forsyth (Advisor)
Anita Mattson (Committee Member)
Jon Parquette (Committee Member)
Chemistry

Recommended Citations

Citations

  • Zhang, Z. (2013). Efforts towards the Total Synthesis of Azaspiracid-3 [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671

    APA Style (7th edition)

  • Zhang, Zhigao. Efforts towards the Total Synthesis of Azaspiracid-3. 2013. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671.

    MLA Style (8th edition)

  • Zhang, Zhigao. "Efforts towards the Total Synthesis of Azaspiracid-3." Doctoral dissertation, Ohio State University, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671

    Chicago Manual of Style (17th edition)

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© 2013, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.
Release 3.2.12