Alexandria Digital Research Library

Development of synthetic methods to access key structural features of tetrapetalone A

Author:
Weaver, Marisa Gail
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:
Tetrapetalone A.
Vinyl Group
Aniline
Nitrogen-Aryl Bond
Diels-Alder
Retro-Diels-Alder
Genres:
Dissertations, Academic and Online resources
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
ARK:
ark:/48907/f3p84bds
ISBN:
9781339472485
Catalog System Number:
990046180240203776
Rights:
Inc.icon only.dark In Copyright
Copyright Holder:
Marisa Weaver
File Description
Access: Public access
Weaver_ucsb_0035D_12875.pdf pdf (Portable Document Format)