Index Catalog // ScholarsArchive@OSU

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:: , Claudia S. Maier, Adrian F. Gombart, Paul R. Blakemore; Journal of Labeled Compounds and

Investigation of Chain Extension Approaches for the Stereoselective Reagent-Controlled Synthesis of alpha-Heteroatom Substituted Alkyl Boronic Esters

Creator:: Barsamian, Adam L.
Abstract:: Two distinct strategies were explored for the enantioselective synthesis of α-heteroatom substituted alkyl boronic esters by stereoselective reagent-controlled homologation using transient chiral carbenoid reagents CHYMX (Y = heteroatom, X = nucleofuge, M = electrofuge). In the first case, a stereospecific reagent-controlled homologation (sStReCH) approach to α-alkoxyalkylboronates using α-metalated S,O- and...
Resource Type:: Dissertation
Full Text:: . Paul R. Blakemore Two distinct strategies were explored for the enantioselective synthesis of α

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

Development of Carbenoid Eliminative Cross-coupling for the Stereocontrolled Synthesis of Trisubstituted Alkenyl Moieties Within Styrenes and 1,3-Dienes

Creator:: Tanpure, Subhash D.
Abstract:: Traditional approaches for the direct preparation of alkenes are unable to fully control either the stereochemical configuration of the carbon-carbon double bond or else the regiochemistry of the substituents surrounding it. The recently introduced concept of carbenoid eliminative cross-coupling (CEXC) offers a remedy to these deficiencies by providing for a...
Resource Type:: Dissertation
Full Text:: : ______________________________________________________ Paul R. Blakemore Traditional approaches for the direct preparation of alkenes are

Broadening the scope of the modified-Julia reaction : a mild and stereoselective method for the synthesis of (Z)-configurated α,β-unsaturated lactones

Creator:: Giesbrecht, Heath Eugene
Abstract:: An intramolecular variant of the modified-Julia olefination was demonstrated by the synthesis of α,β-unsaturated lactones in a mild and (Z)-selective fashion. The lynchpin reagent (benzothiazol-2-sulfonyl) acetic acid was synthesized in a straightforward fashion in 86% overall yield from commercially available 2-mercaptobenzothiazole via conversion to ethyl (benzothiazol-2-ylthio)acetate by base mediated alkylation...
Resource Type:: Masters Thesis
Full Text:: )-Configurated α,β- Unsaturated Lactones Abstract approved: Paul R. Blakemore An intramolecular

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 sparteine alkaloids from a common tetraoxobispidine intermediate

Creator:: Melbardis, John
Abstract:: In previous work (Blakemore et al. Org. Lett. 2005, 7, 4721; Heterocycles 2006, 70, 609), successful elaborations of the lupine alkaloids (±)-α-isosparteine (dl-2) and (±)-β-isosparteine (dl-3) were realized from a common tetraoxobispidine precursor, 3,7-diallyl -2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (93). Herein, the tetraoxobispidine approach to lupine alkaloids was extended to a total synthesis of...
Resource Type:: Masters Thesis
Full Text:: Tetraoxobispidine Intermediate Abstract approved: Paul R. Blakemore In previous work (Blakemore et al

Total Synthesis of Goniomitine : Development of Aminal and α-Amino Radicals in the Synthesis of Nitrogen-Rich Natural Products

Creator:: Vellucci, Jessica K.
Abstract:: Aminal radical intermediates were generated by the method of radical translocation and reacted in C-C bond forming reactions with electronically deficient alkenes (Schiedler et al. Org. Lett. 2012, 14, 6092). Aminal radical intermediates can participate in inter- and intra-molecular reactions using both Bu3SnH and (TMS)₃SiH as hydride donors. Carbon–carbon bonds...
Resource Type:: Dissertation
Full Text:: primarily used for the construction of carbon– heteroatom bonds. In the 1980’s, the application of radical

Part I: Synthetic studies toward the southern portion of Azaspiracid-1; Part II: Total synthesis of amphidinolide B₁ and the proposed structure of amphidinolide B₂

Creator:: Lu, Liang
Abstract:: The structural architecture present in marine toxin azaspiracid - 20 stereocenters, 9 rings, 3 separated spirocenters - has attracted considerable synthetic attention. Our efforts toward the synthesis of azaspiracid have led to the completion of both C₁-C₂₆ northern and C₂₇-C₄₀ southern halves. Herein, the synthesis of southern FGHI ring system...
Resource Type:: Dissertation
Full Text:: extend my appreciation to my committee members, Prof. Paul R. Blakemore, Prof. Kevin P. Gable, Prof

Cis-2,5-diaminobicyclo[2.2.2]octane : a novel C₂-symmetric scaffold for asymmetric catalysis

Creator:: Shaw, Subrata
Abstract:: This thesis describes the development of a new enantioselective synthetic method employing chiral cis-2,5-diaminobicyclo[2.2.2]octane-based organometallic catalysts. The significance of this new method to organic synthesis is illustrated with preparation of enantioenriched products that are transformed to important pharmaceutical agents. Chapter 1 provides a brief historical overview of asymmetric catalysis, especially...
Resource Type:: Dissertation
Full Text:: obliged to Professor Rich G. Carter, Paul R. Blakemore and Kevin P Gable from the Department of Chemistry

ScholarsArchive@OSU

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

Investigation of Chain Extension Approaches for the Stereoselective Reagent-Controlled Synthesis of alpha-Heteroatom Substituted Alkyl Boronic Esters

Development of Methods for Stereoselective Carbon-Carbon Bond Formation

Development of Carbenoid Eliminative Cross-coupling for the Stereocontrolled Synthesis of Trisubstituted Alkenyl Moieties Within Styrenes and 1,3-Dienes

Broadening the scope of the modified-Julia reaction : a mild and stereoselective method for the synthesis of (Z)-configurated α,β-unsaturated lactones

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

Total synthesis of sparteine alkaloids from a common tetraoxobispidine intermediate

Total Synthesis of Goniomitine : Development of Aminal and α-Amino Radicals in the Synthesis of Nitrogen-Rich Natural Products

Part I: Synthetic studies toward the southern portion of Azaspiracid-1; Part II: Total synthesis of amphidinolide B₁ and the proposed structure of amphidinolide B₂

Cis-2,5-diaminobicyclo[2.2.2]octane : a novel C₂-symmetric scaffold for asymmetric catalysis

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