4-membered ring construction in the synthesis of natural products : total synthesis of Ladderane phospholipids and progress toward the synthesis of fomannosin
Abstract/Contents
- Abstract
- Chapter 1 introduces anaerobic ammonium oxidizing (anammox) bacteria and the ladderane lipids, unusual membrane lipids consisting of linearly concatenated cyclobutane motifs. The distinctive biological features and global applications of anammox bacteria are covered, with a focus on anammox catabolism and the possible function of ladderane lipids. The isolation and structural determination of ladderane lipids are outlined, as well as previous and concurrent synthetic efforts. Chapter 2 details our extensive synthetic efforts toward the synthesis of ladderane lipids. Key features of our synthesis of a [5]-ladderane include a scalable synthesis of key building block bicyclo[2.2.0]hex-2-ene, copper(I)-mediated dimerization of this building block, and C--H functionalization of the ladderane core. We also present a synthesis of [3]-ladderane utilizing a [2+2] photocycloaddition with a chiral dihalide, stereospecific alkylzinc addition, and unusual bis-hydrazone oxidative decomposition. Our efforts to determine for the first time the absolute stereochemical configuration of ladderane lipids are also detailed. Finally, the synthesis of two natural and one unnatural ladderane phospholipid as well as biophysical interrogation of synthetic ladderane phospholipids is presented. Chapter 3 describes an ongoing synthetic campaign toward the phytotoxic sesquiterpene fomannosin. Our synthesis requires a challenging quaternary carbon-forming epoxide opening reaction, as well as a cascade cyclization-Ramberg--Bäcklund ring contraction sequence. Efforts toward the completion of the natural product are presented.
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 | 2019; ©2019 |
| Publication date | 2019; 2019 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Cohen, Carolyn Michelle |
|---|---|
| Degree supervisor | Burns, Noah |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Bertozzi, Carolyn R, 1966- |
| Thesis advisor | Du Bois, Justin |
| Degree committee member | Bertozzi, Carolyn R, 1966- |
| Degree committee member | Du Bois, Justin |
| Associated with | Stanford University, Department of Chemistry. |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Carolyn Michelle Cohen. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2019. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2019 by Carolyn Michelle Cohen
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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