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dc.contributor.authorCong, Huanen_US
dc.date.accessioned2018-10-25T12:47:19Z
dc.date.issued2012
dc.date.submitted2012
dc.identifier.otherb38906831
dc.identifier.urihttps://hdl.handle.net/2144/31530
dc.descriptionThesis (Ph.D.)--Boston Universityen_US
dc.descriptionPLEASE NOTE: Boston University Libraries did not receive an Authorization To Manage form for this thesis or dissertation. It is therefore not openly accessible, though it may be available by request. If you are the author or principal advisor of this work and would like to request open access for it, please contact us at open-help@bu.edu. Thank you.en_US
dc.description.abstractSingle electron transfer (SET)-initiated formal [4+2] cycloadditions of 2'-hydroxychalcones have been achieved employing a combination of Lewis acid and electron donor as catalyst. Mechanistic studies using cyclic voltammetry (CV) and deuterium labeling experiments suggested a radical anion-mediated stepwise mechanism. The utility of this methodology was established in the first total synthesis of natural product nicolaioidesin C. A novel silica-supported silver nanoparticle (AgNP) catalyst has been developed as a highly active, reusable, and user-friendly catalyst for Diels-Alder cycloadditions of 2'-hydroxychalcones, as showcased by the first total synthesis of natural product panduratin A. Our work demonstrates results from an interdisciplinary research project involving synthetic methodology development, nanometric material preparation, heterogeneous catalysis, natural product synthesis, and mechanistic studies using various instrumental techniques. Biomimetic, dehydrogenative cycloadditions of 2'-hydroxychalcones have been achieved using a mixture of platinum on activated carbon (Pt/C) and silica-supported silver nanoparticles (AgNP's) catalysts. This heterogeneous multicatalytic protocol converts a prenyl subunit in situ to diene which subsequently reacts with a 2'-hyroxychalcone dienophile to provide Diels-Alder cycloadducts in a single step. Using this methodology, a concise synthesis of the core structure of the natural product brosimone B has been accomplished. Enantioselective cycloadditions of 2'-hydroxychalcones have been established with excellent yields and enantioselectivity. Two optimized catalytic conditions have been developed: the first method utilizes a catalyst system comprised of chiral rare earth metal complex and electron donor; the second approach involves a chiral borate catalyst. The asymmetric total synthesis of natural product (+)-sorocenol B has been pursued.en_US
dc.language.isoen_US
dc.publisherBoston Universityen_US
dc.titleDevelopment and applications of Diels-Alder cycloadditions of 2'-hydroxychalconesen_US
dc.typeThesis/Dissertationen_US
dc.description.embargo2031-01-01
etd.degree.nameDoctor of Philosophyen_US
etd.degree.leveldoctoralen_US
etd.degree.disciplineChemistryen_US
etd.degree.grantorBoston Universityen_US
dc.identifier.barcode11719032086326
dc.identifier.mmsid99196001250001161


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