| dc.identifier.uri | http://hdl.handle.net/1951/59764 | |
| dc.identifier.uri | http://hdl.handle.net/11401/71322 | |
| dc.description.sponsorship | This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree. | en_US |
| dc.format | Monograph | |
| dc.format.medium | Electronic Resource | en_US |
| dc.language.iso | en_US | |
| dc.publisher | The Graduate School, Stony Brook University: Stony Brook, NY. | |
| dc.type | Dissertation | |
| dcterms.abstract | Among methods of asymmetric synthesis, transition-metal catalyzed asymmetric transformation has proven to be a highly efficient and enabling methodology to induce desired chirality. In our laboratory, libraries of novel biphenol-based monodentate phosphoramidite and bidentate diphosphonite ligands have been developed, which are very effective in asymmetric allylic transformations. We present here the application of Pd-catalyzed intramolecular asymmetric allylic amination to the synthesis of enantiopure key intermediates, 1-vinyltetrahydroisoquinolines in the total synthesis of Schulzeines A-C using our diphosphonite ligands. Schulzeines A-C, isolated from a marine sponge, Penares Schulzei, have been identified as a new class of marine natural products, which exhibit potent alpha-glucosidase inhibitory activity making them promising leads for drug development for cancer, diabetes, viral infections and other diseases. We also studied a highly efficient Pd-catalyzed asymmetric tandem allylic alkylation process for the synthesis of an advanced key intermediate to (-)-Huperzine A with excellent enantioseletivity using our phosphoramidite ligands. (-)-Huperzine A, isolated from the plant firmoss, Huperzia serrata, is an acetylcholinesterase (AChE) inhibitor and shows promise in the treatment of Alzheimer's disease and enhance memory. Besides, Pd-catalyzed asymmetric Heck reaction, chiral biphenol-based phosphoric acid mediated asymmetric organocatalysis and Rh-catalyzed [2+2+2+1] cycloaddition of enediynes were investigated and highlighted in the dissertation as well. | |
| dcterms.available | 2013-05-22T17:35:07Z | |
| dcterms.available | 2015-04-24T14:47:02Z | |
| dcterms.contributor | Kerber, Robert C.Goroff, Nancy S.Gupta, Ramesh C.. | en_US |
| dcterms.contributor | Ojima, Iwao | en_US |
| dcterms.creator | Lin, Chi-Feng | |
| dcterms.dateAccepted | 2013-05-22T17:35:07Z | |
| dcterms.dateAccepted | 2015-04-24T14:47:02Z | |
| dcterms.dateSubmitted | 2013-05-22T17:35:07Z | |
| dcterms.dateSubmitted | 2015-04-24T14:47:02Z | |
| dcterms.description | Department of Chemistry | en_US |
| dcterms.extent | 349 pg. | en_US |
| dcterms.format | Application/PDF | en_US |
| dcterms.format | Monograph | |
| dcterms.identifier | http://hdl.handle.net/1951/59764 | |
| dcterms.identifier | Lin_grad.sunysb_0771E_11050 | en_US |
| dcterms.identifier | http://hdl.handle.net/11401/71322 | |
| dcterms.issued | 2012-08-01 | |
| dcterms.language | en_US | |
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Previous issue date: 1 | en |
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Previous issue date: 1 | en |
| dcterms.publisher | The Graduate School, Stony Brook University: Stony Brook, NY. | |
| dcterms.subject | Organic chemistry | |
| dcterms.title | Development of Enantiopure Biphenol-Based Phosphorus Ligand Libraries and Their Applications to Palladium-Catalyzed Asymmetric Transformations | |
| dcterms.type | Dissertation | |
