Application of enantioselective dihalogenation to the total synthesis of terpene natural products
Abstract/Contents
- Abstract
- 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.
Description
| Type of resource | text |
|---|---|
| Form | electronic resource; remote; computer; online resource |
| Extent | 1 online resource. |
| Place | California |
| Place | [Stanford, California] |
| Publisher | [Stanford University] |
| Copyright date | 2018; ©2018 |
| Publication date | 2018; 2018 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Bucher, Cyril |
|---|---|
| Degree supervisor | Burns, Noah |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Du Bois, Justin |
| Thesis advisor | Kanan, Matthew William, 1978- |
| Degree committee member | Du Bois, Justin |
| Degree committee member | Kanan, Matthew William, 1978- |
| Associated with | Stanford University, Department of Chemistry. |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Cyril Bucher. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2018. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2018 by Cyril Bucher
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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