Type
Text
Type
Thesis
Advisor
Ngai, Ming-Yu | Parker, Kathlyn A. | Rushton, Gregory.
Date
2017-08-01
Keywords
Model study | Organic chemistry | Total synthesis
Department
Department of Chemistry.
Language
en_US
Source
This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree
Identifier
http://hdl.handle.net/11401/78195
Publisher
The Graduate School, Stony Brook University: Stony Brook, NY.
Format
application/pdf
Abstract
Gukulenin A, a tetraterpene, contains a unique bis-tropolone moiety, and exhibits potent cytotoxicity against various cell lines (human pharynx cancer FaDu, colon cancer HCT-116, renal cancer SN12C, stomach cancer MKN45). Developing a straightforward and concise synthesis of gukulenin A from easily available starting materials is meaningful for synthetic chemistry as well as drug discovery. In our research, we proposed that gukulenin A could be assembled via the four types of dimerization from three different substrates. In this project, we focused on the synthesis of 4-methyltropolone as the substrate for oxidative coupling, and (Z)-1-oxo-1-phenylpenta-2,4-dien-2-yl acetate as the model for a new Michael addition approach. At this point, we have obtained 4-methyltropolone with one of its isomers, and we have successfully made (Z)-1-oxo-1-phenylpenta-2,4-dien-2-yl acetate and tested the Michael-type dimerization under basic condition. | 61 pages
Recommended Citation
Su, Siyuan, "Model Compounds for the Biomimetic Synthesis of Gukulenins" (2017). Stony Brook Theses and Dissertations Collection, 2006-2020 (closed to submissions). 3690.
https://commons.library.stonybrook.edu/stony-brook-theses-and-dissertations-collection/3690