Total Synthesis of Tetrapetalone A
- Degree Grantor:
- University of California, Santa Barbara. Chemistry and Biochemistry
- Degree Supervisor:
- Thomas R. R. Pettus
- Place of Publication:
- [Santa Barbara, Calif.]
- Publisher:
- University of California, Santa Barbara
- Creation Date:
- 2015
- Issued Date:
- 2015
- Topics:
- Chemistry, Organic
- Keywords:
- Total synthesis,
Natural product - Genres:
- Online resources and Dissertations, Academic
- Dissertation:
- Ph.D.--University of California, Santa Barbara, 2015
- Description:
The natural product tetrapetalone A has attracted lots of synthetic efforts since its isolation in 2003. The main project is to achieve its total synthesis in the laboratory. Our strategy features a concise preparation of the tetramic acid core, a classic Heck reaction, an aldol condensation, a changeling regioselective quaternization, a Friedel-Crafts reaction, and an oxidative dearomatization.
Overall, two natural products have been involved in this project, which are palau'imide and tetrapetalone A. Three methods have been developed surrounding this project, including the SmI2-mediated cyclization, the Diels-Alder construction of meta-amino phenols, and the aldol reaction of tetramic acids. Four side projects have been generated. The aldol reaction of tetramic acids has been published. The rest three are currently being studied in our laboratory, including a new vinylation strategy, an asymmetric aldol reaction of tetramic acids, and some medicinal studies.
- Physical Description:
- 1 online resource (52 pages)
- Format:
- Text
- Collection(s):
- UCSB electronic theses and dissertations
- Other Versions:
- http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqm&rft_dat=xri:pqdiss:3689872
- ARK:
- ark:/48907/f35h7dfz
- ISBN:
- 9781321695557
- Catalog System Number:
- 990045119230203776
- Copyright:
- WENJU BAI, 2014
- Rights:
In Copyright
- Copyright Holder:
- WENJU BAI
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