Studies on the syntheses and biophysical characterizations of archaeal tetraether lipids and the syntheses of pyrroloiminoquinone alkaloids
Abstract/Contents
- Abstract
- Archaeal extremophiles produce exotic lipid structures believed to enable survival under conditions lethal to most other life. These lipids, known as glycerol dibiphytanyl glycerol tetraethers (GDGT's), have attracted significant scientific interest. However, acquisition of these lipids from their producing organisms is not feasible. Thus, total synthesis represents the best method toward accessing these structures. Our lab has developed the shortest enantioselective synthesis of GDGT-0 relying on a global asymmetric hydrogenation and a formal macroetherification. Using this approach, we have prepared derivatives of this lipid and have begun biophysical characterizations of these compound. Furthermore, efforts are presently underway to synthesize the cycloalkane containing members of the family. The pyrroloiminoquinone alkaloids are a class of natural products principally found in marine organisms. These compounds have demonstrated a wide range of bioactivities including potent anticancer activity. Synthetic access to these structures would provide material for further investigations into their therapeutic potential. Our group developed the first catalytic asymmetric approach toward the discorhabdin pyrroloiminoquinone alkaloids. Our approach leveraged a C-H functionalization platform to rapidly assemble the core of these natural products from tryptamine. An asymmetric Morita-Baylis-Hillman strategy enabled a late-stage bromination to access these natural products in an enantioselective fashion.
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 | 2022; ©2022 |
| Publication date | 2022; 2022 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Falk, Isaac Doran |
|---|---|
| Degree supervisor | Burns, Noah |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Boxer, Steven G. (Steven George), 1947- |
| Thesis advisor | Du Bois, Justin |
| Degree committee member | Boxer, Steven G. (Steven George), 1947- |
| Degree committee member | Du Bois, Justin |
| Associated with | Stanford University, Department of Chemistry |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Isaac Falk. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2022. |
| Location | https://purl.stanford.edu/ms201vr6754 |
Access conditions
- Copyright
- © 2022 by Isaac Doran Falk
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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