Development of synthetic methods to access key structural features of tetrapetalone A
- Degree Grantor:
- University of California, Santa Barbara. Chemistry
- 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:
- Organic chemistry
- Keywords:
- Vinyl Group,
Tetrapetalone A.,
Nitrogen-Aryl Bond,
Retro-Diels-Alder,
Diels-Alder, and
Aniline - Genres:
- Online resources and Dissertations, Academic
- Dissertation:
- Ph.D.--University of California, Santa Barbara, 2015
- Description:
The tetracyclic natural product, tetrapetalone A has eluded chemists since its isolation in 2002. The complex structural features of this natural product provide a platform from which new synthetic methods can be developed. One approach to build tetrapetalone includes formation of a Nitrogen-Aryl bond. Despite the prevalence of this bond connection in natural and pharmaceutical compounds, previous methods to form Nitrogen-Aryl bonds were not applicable in our approach to the tetrapetalone A scaffold. To overcome this limitation and provide a different route to access compounds containing Nitrogen-Aryl bonds, we approached the problem with a different strategy. This divergent strategy relies upon distinct deprotonation conditions of a cyclic vinylogous amide to afford regioisomeric dienes. Each diene can then undergo a tandem Diels-Alder and retro-Diels-Alder sequence with a variety of acetylenic dienophiles to afford a range of multi-substituted aromatic products containing Nitrogen-Aryl bonds. The scope of this method and its application toward tetrapetalone A will be discussed. While investigating different synthetic approaches, our group also probed the reactivity of the tetramic acid C-5 position. When our group encountered limitations among the current methods to install vinyl groups at the C-5 position we turned to develop a more general vinylation strategy. Our progress toward a "vinylation reagent" is reported and future directions will be discussed.
- Physical Description:
- 1 online resource (169 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:10011420
- ARK:
- ark:/48907/f3p84bds
- ISBN:
- 9781339472485
- Catalog System Number:
- 990046180240203776
- Copyright:
- Marisa Weaver, 2015
- Rights:
- In Copyright
- Copyright Holder:
- Marisa Weaver
File | Description |
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Access: Public access | |
Weaver_ucsb_0035D_12875.pdf | pdf (Portable Document Format) |