{"@context":"http://iiif.io/api/presentation/2/context.json","@id":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/manifest.json","@type":"sc:Manifest","label":"Part I. Studies of Stereoselective C-H \nAmination, Part II. Synthetic Studies of Edaxadiene, Part III. Studies \ntowards the Synthesis of Alchivemycin A, Part IV. The Formal Synthesis \nof (-)-Englerin A by RRCM and Etherification","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/1951/59749"},{"label":"dc.language.iso","value":"en_US"},{"label":"dc.publisher","value":"The Graduate School, Stony Brook University: Stony Brook, NY."},{"label":"dcterms.abstract","value":"Part I. \nVarious polysaccharides and glycosidic antibiotics including \nanthracycline and vancomycin have been widely used to treat cancer or \ninfection. Amino sugars are often found in their structures and play an \nimportant role in biological activities. C-H amination is one of \nvaluable methods to streamline the synthesis of C-N bond. Regio-, \nstereoselective C-H amination has been studied to produce useful amino \nsugars from glycals and alkynol carbamates.  Part II. Edaxadiene was \nconsidered as a new diterpene that had biological activities to inhibit \nthe infection process of Mycobacterium tuberculosis. We describe a \ndesign to access a bicyclic backbone, which is the core structure of \nthis compound by an intramolecular Diels-Alder (IMDA) reaction.  Part \nIII. Progress toward the synthesis of a key moiety of alchivemycin A, \nwhich was isolated from a plant-derived actinomycete Streptomyces sp and \ndisplayed selective and potent antibiotic activity against Micrococcus \nluteus, has been focused on the construction of a bicyclic structure by \nthe IMDA reaction.  Part IV. (-)-Englerin A is a natural product from \nphyllathus engleri, a plant common in east Africa. It showed an \ninteresting biological activity in its ability to inhibit the growth of \nkidney cancer cell lines in the NCI-60 screen. The useful bioactivity \nand unique structure of (-)-englerin A have inspired many scientists to \ndevelop synthetic approaches to understand the structure-activity \nrelationship (SAR). We reported the formal synthesis of (-)-englerin A \nand established an efficient synthetic route by a relay ring closing \nmetathesis (RRCM) reaction and etherification. This study includes the \nefficient opening of the epoxide ring of a \u0392-substituted \n\u0391-epoxy alcohol under the lithium acetylide reagent, the relay \nene-yne-ene metathesis method for the preparation of a diene that is \ndisubstituted on both ends, and the transannular stereo- and \nregio-specific oxymercuration of the C-6, C-7 olefin in the guaiane ring \nsystem."},{"label":"dcterms.available","value":"2015-04-24T14:46:59Z"},{"label":"dcterms.contributor","value":"Parker, Kathlyn A"},{"label":"dcterms.creator","value":"Lee, Jungyong"},{"label":"dcterms.dateAccepted","value":"2013-05-22T17:35:00Z"},{"label":"dcterms.dateSubmitted","value":"2015-04-24T14:46:59Z"},{"label":"dcterms.description","value":"Department of Chemistry"},{"label":"dcterms.extent","value":"370 pg."},{"label":"dcterms.format","value":"Monograph"},{"label":"dcterms.identifier","value":"http://hdl.handle.net/1951/59749"},{"label":"dcterms.issued","value":"2012-08-01"},{"label":"dcterms.language","value":"en_US"},{"label":"dcterms.provenance","value":"Made available in DSpace on 2013-05-22T17:35:00Z (GMT). No. of bitstreams: 1\nLee_grad.sunysb_0771E_11111.pdf: 12674205 bytes, checksum: e20f450df961b2cb02890de63eaea785 (MD5)\n  Previous issue date:    1"},{"label":"dcterms.publisher","value":"The Graduate School, Stony Brook University: Stony Brook, NY."},{"label":"dcterms.subject","value":"Chemistry--Organic \nchemistry"},{"label":"dcterms.title","value":"Part I. Studies of Stereoselective C-H \nAmination, Part II. Synthetic Studies of Edaxadiene, Part III. Studies \ntowards the Synthesis of Alchivemycin A, Part IV. The Formal Synthesis \nof (-)-Englerin A by RRCM and Etherification"},{"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/2/11%2F75%2F82%2F117582413874975011987662921028678835337/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/2/11%2F75%2F82%2F117582413874975011987662921028678835337","profile":"http://iiif.io/api/image/2/level2.json"}},"on":"https://repo.library.stonybrook.edu/cantaloupe/iiif/2/canvas/page-1.json"}]}]}]}