A Synthetic Approach Towards Paecilospirone
- 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:
- 2013
- Issued Date:
- 2013
- Topics:
- Chemistry, Organic and Chemistry, General
- Genres:
- Online resources and Dissertations, Academic
- Dissertation:
- Ph.D.--University of California, Santa Barbara, 2013
- Description:
Our research focuses on the total synthesis of naturally occurring highly oxidized and densely functionalized carbon skeletons. The generation of dearomatized intermediates and o-quinone methides enable the rapid manipulation and derivatization of aromatic cores. o-Quinone methides in particular undergo a variety of reactions, but in the presence of enol ethers cycloaddition reactions predominate, which enable access to complex spiroketal derivatives. The use of this technology enables the generation of spiroketals in a kinetic fashion, not possible through traditional thermodynamic ketalizations. Herein, we will overview our studies towards finding an appropriate o-quinone methide precursor and demonstrate the application of this methodology towards the total synthesis of paecilospirone, a marine natural product whose unique chroman spiroketal core had not previously been encountered in nature prior to its isolation.
- Physical Description:
- 1 online resource (323 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:3596089
- ARK:
- ark:/48907/f3n877rv
- ISBN:
- 9781303424885
- Catalog System Number:
- 990040770080203776
- Copyright:
- G. Burnett IV, 2013
- Rights:
In Copyright
- Copyright Holder:
- G. Burnett IV
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