Index Catalog // ScholarsArchive@OSU

Atropisomeric 8,8'-biquinolyl derivatives : synthesis, properties and applications

Creator:: Milicevic, Selena D.
Abstract:: 7,7'-Dihydroxy-8,8'-biquinolyl (azaBINOL) was prepared from 7-hydroxyquinoline via N,N-dimethyl O-quinol-7-yl carbamate by directed ortho-metallation followed by FeCl₃-mediated oxidative coupling of the 8-lithioquinoline intermediate. Saponification of the resulting dicarbamate provided crystalline (±)-azaBINOL in 56% overall yield. 6,6'-Bis(dimethylaminocarbonyl)-7,7'-dihydroxy-8,8´-biquinolyl was prepared from the same dicarbamate by a double anionic-Fries rearrangement in 43% yield. 7,7'-Bis(diethylamino-carbonyloxy)-6,6'-diiodo-8,8´-biquinolyl...
Resource Type:: Dissertation
Full Text:: Paul R. Blakemore 7,7´-Dihydroxy-8,8´-biquinolyl (azaBINOL) was prepared from 7-hydroxyquinoline

Towards the Perfect Marriage Between Theory and Experiments in Drug Discovery and Synthesis : Insights into Structure Determination of Complex Natural Products and Mechanistic Understandings of Lactam Synthesis

Creator:: Snyder, Kevin M.
Abstract:: In this report, three studies are presented that aid in the development of drug discovery and their synthesis. In each, the importance of the marriage between computations and experiments is highlighted. Continued efforts in this vein are essential for future efforts towards improving human health. The first case study investigated...
Resource Type:: Masters Thesis
Full Text:: Synthesis Abstract approved: ______________________________________________________ Paul Ha

Stereoselective synthesis & application of enantioenriched main group α-haloalkyl organometal reagents

Creator:: Emerson, Christopher R.
Abstract:: Sulfoxide-ligand exchange (SLE) and asymmetric halogen-metal exchange (AHME) processes were separately examined for the enantioselective synthesis of functionalized alpha-haloalkylmetal (carbenoid) reagents. Carbenoids derived from SLE were used to effect stereospecific reagent-controlled homologation (StReCH) of boronic esters and those generated via AHME were engaged in Darzens-type chemistry with aldehydes. Abstract for...
Resource Type:: Dissertation

Progress Towards the Total Synthesis of Bazzanin K

Creator:: Salvo, Patrick
Abstract:: Molecular chirality plays a critical role in chemistry, biology, and medicine. To study and better understand conformational chirality, it is necessary to obtain structurally interesting molecules that exhibit this form of chirality. Our lab utilizes total synthesis and methodological development to obtain conformationally chiral natural products of interest. We believe...
Resource Type:: Masters Thesis
Full Text:: . Title: Progress Towards the Total Synthesis of Bazzanin K. Abstract approved

Development of Methods for Stereoselective Carbon-Carbon Bond Formation

Creator:: Wu, Zhenhua
Abstract:: Three distinct methods to achieve the stereoselective synthesis of carbon-carbon bonds were investigated, encompassing: (i) the formation of axially chiral biaryl molecules by enantioselective Suzuki cross-coupling, (ii) the synthesis of α-phenylalkylboronic esters by enantioselective chain extension, and (iii) the stereospecific synthesis of alkenes by eliminative cross-coupling of enantioenriched sp³-hybridized carbenoids....
Resource Type:: Dissertation
Full Text:: : ______________________________________________________ Paul R. Blakemore Three distinct methods to achieve the stereoselective synthesis of

Scaffold reactivity and large scale Synthesis of organocatalyzed Yamada-Otani Condensation product and investigation of the synthesis and properties of axially chiral 8,8'-biquinolyls and 8-(naphtha-1-yl)quinolines

Creator:: Banerjee, Somdev
Abstract:: In Part I, (4S,5R)-4,5-dimethyl-4-phenylcyclohex-2-enone (19a) was prepared in 73% yield with high enantio- and diastereo-selectivity (er > 98:2, dr > 20:1) on a multigram scale by a Yamada-Otani condensation between (E)-pent-3-en-2-one and 2-phenylpropanal catalyzed by a sulfonimide derivative of (S)-proline (18, HuaCat®). Synthetically useful transformations of the cyclohexenone product 19a...
Resource Type:: Dissertation
Full Text:: Abstract approved: Paul R. Blakemore In Part I, (4S,5R)-4,5-dimethyl-4-phenylcyclohex-2-enone

Analysis of the mechanism of sulfoxide-lithium exchange and the reactive intermediate in stereospecific reagent-controlled homologation (StReCH)

Creator:: Hoyt, Amanda
Abstract:: The stereospecific reagent-controlled homologation (StReCH) of boronic esters with enantioenriched carbenoid species generated in situ by the addition of organolithium initiators to stereodefined α-chloroalkyl aryl sulfoxides was previously reported. The reaction of an organolithium with an α-chloroalkyl aryl sulfoxide ostensibly generates an α-chloroalkyllithium via sulfoxide-lithium exchange; however, the true nature...
Resource Type:: Masters Thesis
Full Text:: : Paul R. Blakemore The stereospecific reagent-controlled homologation (StReCH) of boronic esters

Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

Creator:: Cao, Yang
Abstract:: The bimolecular reaction of two carbenoid species resulting in the formation of a carbon-carbon double bond (pi-system), referred to herein as carbenoid eliminative cross-coupling (CEXC), involves a series of three fundamental steps: (i) ate-complex formation (transmetalation), (ii) 1,2-metalate rearrangement, and (iii) beta-elimination. All three steps are stereospecific and so the...
Resource Type:: Dissertation
Full Text:: Paul R. Blakemore The bimolecular reaction of two carbenoid species resulting in the formation

Synthesis of novel ambifunctional atropisomeric 2,2',6,6'-tetrasubstituted biphenyls and investigation of their properties and organocatalytic activity

Creator:: Sephton, Mark Alan
Abstract:: Ambifunctional axially chiral 2,2',6,6'-tetrasubstituted biphenyls containing nucleophilic (or basic) functional groups juxtaposed with hydrogen-bond donors were synthesized and their properties studied. Applications for the prepared biaryls as potential organocatalysts for enantioselective carbon-carbon bond forming reactions were examined. Processes investigated included: aldol, Michael, nitroaldol (Henry), and Baylis-Hillman reactions. The novel amidoamine...
Resource Type:: Dissertation
Full Text:: Activity. Abstract approved: Paul R. Blakemore Ambifunctional axially chiral 2,2

Total Synthesis of Isotopologues of Xanthohumol and its Congeners for Biological Studies

Creator:: Plagmann, Layhna S.
Abstract:: Xanthohumol [XN, (E)-6´-methoxy-3´-(3-methylbuten-2-yl)-2´,4´,4´´-trihydroxychalcone], the principal prenylated chalcone from hops, and its 2,3-dihydro- (DXN) and O6-desmethyl-2,3-dihydro- (DDXN) congeners, are of potential utility for the amelioration of metabolic syndrome; however, their complex bioactivity profiles cannot be properly studied and understood without access to appropriately produced synthetic materials. In the first part of...
Resource Type:: Masters Thesis
Full Text:: Isotopologues of Xanthohumol and its Congeners for Biological Studies Abstract approved: Paul

ScholarsArchive@OSU

Atropisomeric 8,8'-biquinolyl derivatives : synthesis, properties and applications

Towards the Perfect Marriage Between Theory and Experiments in Drug Discovery and Synthesis : Insights into Structure Determination of Complex Natural Products and Mechanistic Understandings of Lactam Synthesis

Stereoselective synthesis & application of enantioenriched main group α-haloalkyl organometal reagents

Progress Towards the Total Synthesis of Bazzanin K

Development of Methods for Stereoselective Carbon-Carbon Bond Formation

Scaffold reactivity and large scale Synthesis of organocatalyzed Yamada-Otani Condensation product and investigation of the synthesis and properties of axially chiral 8,8'-biquinolyls and 8-(naphtha-1-yl)quinolines

Analysis of the mechanism of sulfoxide-lithium exchange and the reactive intermediate in stereospecific reagent-controlled homologation (StReCH)

Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

Synthesis of novel ambifunctional atropisomeric 2,2',6,6'-tetrasubstituted biphenyls and investigation of their properties and organocatalytic activity

Total Synthesis of Isotopologues of Xanthohumol and its Congeners for Biological Studies

Limit your search

Academic Affiliation

Advisor

Commencement Year

Committee Member

Creator

Contributor

Date

Decade

Degree Field

Degree Level

Degree Name

File Format

Language

License

Non-Academic Affiliation

Peer Reviewed

Resource Type

Rights Statement

Subject

Search Constraints

Search Results

Limit your search