Alexandria Digital Research Library

Total Synthesis of Tetrapetalone A

Author:
Bai, Wenju
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
ARK:
ark:/48907/f35h7dfz
ISBN:
9781321695557
Catalog System Number:
990045119230203776
Rights:
Inc.icon only.dark In Copyright
Copyright Holder:
WENJU BAI
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