{"@context":"http://iiif.io/api/presentation/2/context.json","@id":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/manifest.json","@type":"sc:Manifest","label":"Development of Enantiopure Biphenol-Based Phosphorus Ligand Libraries and Their Applications to Palladium-Catalyzed Asymmetric Transformations","metadata":[{"label":"dc.description.sponsorship","value":"This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree."},{"label":"dc.format","value":"Monograph"},{"label":"dc.format.medium","value":"Electronic Resource"},{"label":"dc.identifier.uri","value":"http://hdl.handle.net/1951/59764"},{"label":"dc.language.iso","value":"en_US"},{"label":"dc.publisher","value":"The Graduate School, Stony Brook University: Stony Brook, NY."},{"label":"dcterms.abstract","value":"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."},{"label":"dcterms.available","value":"2015-04-24T14:47:02Z"},{"label":"dcterms.contributor","value":"Kerber, Robert C.Goroff, Nancy S.Gupta, Ramesh C.."},{"label":"dcterms.creator","value":"Lin, Chi-Feng"},{"label":"dcterms.dateAccepted","value":"2015-04-24T14:47:02Z"},{"label":"dcterms.dateSubmitted","value":"2013-05-22T17:35:07Z"},{"label":"dcterms.description","value":"Department of Chemistry"},{"label":"dcterms.extent","value":"349 pg."},{"label":"dcterms.format","value":"Monograph"},{"label":"dcterms.identifier","value":"http://hdl.handle.net/1951/59764"},{"label":"dcterms.issued","value":"2012-08-01"},{"label":"dcterms.language","value":"en_US"},{"label":"dcterms.provenance","value":"Made available in DSpace on 2015-04-24T14:47:02Z (GMT). No. of bitstreams: 3\nLin_grad.sunysb_0771E_11050.pdf.jpg: 1894 bytes, checksum: a6009c46e6ec8251b348085684cba80d (MD5)\nLin_grad.sunysb_0771E_11050.pdf.txt: 433083 bytes, checksum: 41f4547763becea264615f9fe96b20cb (MD5)\nLin_grad.sunysb_0771E_11050.pdf: 3878432 bytes, checksum: 438aa2b305c0866d7ca0e276be0540df (MD5)\n  Previous issue date:    1"},{"label":"dcterms.publisher","value":"The Graduate School, Stony Brook University: Stony Brook, NY."},{"label":"dcterms.subject","value":"Organic chemistry"},{"label":"dcterms.title","value":"Development of Enantiopure Biphenol-Based Phosphorus Ligand Libraries and Their Applications to Palladium-Catalyzed Asymmetric Transformations"},{"label":"dcterms.type","value":"Dissertation"},{"label":"dc.type","value":"Dissertation"}],"description":"This manifest was generated dynamically","viewingDirection":"left-to-right","sequences":[{"@type":"sc:Sequence","canvases":[{"@id":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/canvas/page-1.json","@type":"sc:Canvas","label":"Page 1","height":1650,"width":1275,"images":[{"@type":"oa:Annotation","motivation":"sc:painting","resource":{"@id":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/46%2F32%2F28%2F46322861797014523215629263741794201491/full/full/0/default.jpg","@type":"dctypes:Image","format":"image/jpeg","height":1650,"width":1275,"service":{"@context":"http://iiif.io/api/image/2/context.json","@id":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/46%2F32%2F28%2F46322861797014523215629263741794201491","profile":"http://iiif.io/api/image/2/level2.json"}},"on":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/canvas/page-1.json"}]}]}]}