Total synthesis of (-)-Flueggeacosine C.
| dc.contributor.advisor | Wood, John L. (John Louis) | |
| dc.creator | Liu, Lin, 1992- | |
| dc.date.accessioned | 2024-07-30T12:43:36Z | |
| dc.date.available | 2024-07-30T12:43:36Z | |
| dc.date.created | 2023-12 | |
| dc.date.issued | 2023-12 | |
| dc.date.submitted | December 2023 | |
| dc.date.updated | 2024-07-30T12:43:36Z | |
| dc.description.abstract | Ying Wang and co-workers reported the isolation of Flueggeacosines A-C from Flueggea suffruticosa in 2018. Flueggeacosine C showed potential bioactivities to promote the differentiation of Neuro-2a cells. It is a heterodimer of securinine-type and benzoquinolizidine alkaloids. This unprecedented skeleton makes it an interesting and challenging target to synthesize. The efforts described herin continue to broad the scope of acyloxynitroso ring expansion chemistry, a process which serves as the key reaction in assembling the amide core found in flueggeacosinsâs benzoquinolizidine fragment. In addition, we describe the development of a novel intramolecular Diels-Alder reaction to construct the butenolide / [2,2,2] azabicyclic core in one step. The latter chemistry proved very efficient, allowing the preparation of material on gram-scale. In completing this fragment, a copper-catalyzed diastereoselective hydration reaction was employed to efficiently introduce the secondary alcohol in a regio- and stereoselective fashion. Finally, a LiebeskindâSrogl reaction served to couple the two fragments. Given that the fragments were both generated as racemates and coupling gave rise to inseparable mixture of diastereomers, we turned to chiral separations technology to provide the coupling partners in enantioenriched form. Following separation, the absolute stereochemistry of benzoquinalizadine fragment was assigned via chemical correlation. Coupling of the resolved materials furnished the natural product in an overall 13 step sequence from commercially available compounds. | |
| dc.format.mimetype | application/pdf | |
| dc.identifier.uri | ||
| dc.identifier.uri | https://hdl.handle.net/2104/12869 | |
| dc.language.iso | English | |
| dc.rights.accessrights | No access â contact librarywebmaster@baylor.edu | |
| dc.title | Total synthesis of (-)-Flueggeacosine C. | |
| dc.type | Thesis | |
| dc.type.material | text | |
| local.embargo.lift | 2028-12-01 | |
| local.embargo.terms | 2028-12-01 | |
| thesis.degree.department | Baylor University. Dept. of Chemistry & Biochemistry. | |
| thesis.degree.grantor | Baylor University | |
| thesis.degree.name | Ph.D. | |
| thesis.degree.program | Chemistry | |
| thesis.degree.school | Baylor University |
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