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Application of enantioselective dihalogenation to the total synthesis of terpene natural products
Bucher, Cyril[Stanford, California] : [Stanford University], 2018.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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F13-CHEM-35-04 : Synthetic and Physical Organic Chemistry. 2013 Fall
Bucher, CyrilStanford (Calif.), 2013The structure and reactivity of mono- and polyfunctionalized molecules; retrosynthetic analysis and multi-step chemical synthesis. Course will emphasize deductive logic and reasoning skills through conceptual learning. Students gain an appreciation for the profound impact of organic chemistry on humankind in fields ranging from biology and medicine to gastronomy, agriculture, and materials science. A three hour lab section provides hands on experience with modern chemical methods for preparative and analytical chemistry. Prerequisite: Chem 33
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F13-CHEM-35-05 : Synthetic and Physical Organic Chemistry. 2013 Fall
Bucher, CyrilStanford (Calif.), 2013The structure and reactivity of mono- and polyfunctionalized molecules; retrosynthetic analysis and multi-step chemical synthesis. Course will emphasize deductive logic and reasoning skills through conceptual learning. Students gain an appreciation for the profound impact of organic chemistry on humankind in fields ranging from biology and medicine to gastronomy, agriculture, and materials science. A three hour lab section provides hands on experience with modern chemical methods for preparative and analytical chemistry. Prerequisite: Chem 33
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