Stereoselective synthesis of N-heterocycles enabled by tertiary amine catalysis and synthetic efforts towards C-ring synthons of rameswaralide.
| dc.contributor.advisor | Romo, Daniel. | |
| dc.creator | Kong, Weixu, 1992- | |
| dc.date.accessioned | 2018-01-25T14:29:55Z | |
| dc.date.available | 2018-01-25T14:29:55Z | |
| dc.date.created | 2017-12 | |
| dc.date.issued | 2017-09-18 | |
| dc.date.submitted | December 2017 | |
| dc.date.updated | 2018-01-25T14:29:55Z | |
| dc.description.abstract | Extensions of the nucleophile catalyzed aldol lactonization (NCAL) of keto acids, previously developed for the synthesis of carbocycle-fused β-lactones, are described to access a series of N-heterocycle-fused β-lactones. Pyrrolidine- and piperidine-fused tricyclic β-lactones were successfully prepared in moderate to good yields and with high diastereoselectivity. A catalytic, enantioselective process was developed for the synthesis of bicyclic N-heterocycle-fused β-lactones in high enantiomeric purity. The utility of these adducts was explored briefly through deprotection of the N-tosyl group and functionalization of the β-lactones. The utility of chiral α, β unsaturated acylammonium salts, derived from carbonic anhydrides and chiral isothiourea catalysts, was extended to aza-Michael initiated organocascades, delivering pyrazolidinones and 1,5-benzodiazepinones. Finally, efforts toward the synthesis of C ring synthons useful for the total synthesis of rameswaralide were pursued. Key strategies involved a C-H oxygenation and γ-alkylation of (R)-carvone leading to serviceable intermediates for a total synthesis of this natural product. | |
| dc.format.mimetype | application/pdf | |
| dc.identifier.uri | http://hdl.handle.net/2104/10194 | |
| dc.rights.accessrights | Worldwide access. | |
| dc.rights.accessrights | Access changed 5/23/23. | |
| dc.subject | Tertiary amine catalysis. N-heterocycles synthesis. | |
| dc.title | Stereoselective synthesis of N-heterocycles enabled by tertiary amine catalysis and synthetic efforts towards C-ring synthons of rameswaralide. | |
| dc.type | Thesis | |
| dc.type.material | text | |
| local.embargo.lift | 2022-12-01 | |
| local.embargo.terms | 2022-12-01 | |
| thesis.degree.department | Baylor University. Dept. of Chemistry & Biochemistry. | |
| thesis.degree.grantor | Baylor University | |
| thesis.degree.level | Masters | |
| thesis.degree.name | M.S. |
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