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Toward Total Synthesis of Azaspiracid-3 and Azaspiracid-34

Okumu, Antony A.
http://rave.ohiolink.edu/etdc/view?acc_num=osu1461282755

Abstract Details

2016, Doctor of Philosophy, Ohio State University, Chemistry.
Azaspiracids are a class of marine natural products that accumulate in shellfish. Azaspiracid 1 was first reported in 1995 in the Netherlands after a poisoning incident and this led to its isolation and structure elucidation in 1998. Biological activities of azaspiracids are not fully known and further studies are necessary. They occur in scarce quantities in nature and therefore synthesis in the laboratory would facilitate these studies. There is need to examine their molecular pharmacology and to develop better means of their detection. The C1-C21 (ABCD) and C22-C40 (FGHI) fragments have been synthesized in our lab. The key reactions toward these synthesis were Nozaki-Hiyama-Kishi reaction, the Chelation controlled Mukaiyama aldol reaction, and trioxadispiroketalization under thermodynamic conditions. Earlier work in the group also involved gold-catalyzed trioxadispiroketalization. Syntheses of analogs of azaspiracids are necessary for toxicological studies, and to enable better environmental regulation. The highlight of the synthesis of the ABCD fragment of azaspiracid 34 was a Wittig olefination, selective conjugate reduction that was carried out at different stages of synthesis, and NHK coupling.
Craig Forsyth (Advisor)
220 p.
Chemistry; Organic Chemistry
Azaspiracid; Natural Product Synthesis; NHK Coupling

Recommended Citations

Citations

  • Okumu, A. A. (2016). Toward Total Synthesis of Azaspiracid-3 and Azaspiracid-34 [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1461282755

    APA Style (7th edition)

  • Okumu, Antony. Toward Total Synthesis of Azaspiracid-3 and Azaspiracid-34. 2016. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1461282755.

    MLA Style (8th edition)

  • Okumu, Antony. "Toward Total Synthesis of Azaspiracid-3 and Azaspiracid-34." Doctoral dissertation, Ohio State University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=osu1461282755

    Chicago Manual of Style (17th edition)

osu1461282755
568
© 2016, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.