Application of enantioselective dihalogenation to the total synthesis of terpene natural products
- Cyril Bucher.
- [Stanford, California] : [Stanford University], 2018.
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- 1 online resource.
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|3781 2018 B||In-library use|
- ["Halogenated natural products are ubiquitous and in many cases display promising biomedical potential. Due to the scarcity of methods for the stereoselective incorporation of halides into organic substrates and the difficulty of isolation from nature, access to most members for anticancer screening is severely limited. We were able to leverage an advancement made in our laboratory, which allows for chemo-, regio-, and enantioselective synthesis of vicinal dihalide products, toward the stereoselective total synthesis of several polyhalogenated natural products. One of these compounds, halomon, was tested on the Bassik laboratory target identification screen, which identified an interesting pathway that serves to export the drug from the cancer cell. We have further shown that enriched dihalides can act as novel forms of chiral, removable auxiliaries that enable synthesis of stereocenters that are difficult to access with traditional methods."]
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- Submitted to the Department of Chemistry.
- Thesis Ph.D. Stanford University 2018.
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