Index Catalog // ScholarsArchive@OSU

Regioselective Synthesis of Substituted Phenols, Benzenes, Benzofuranones and Benzofurans and Synthesis of Homoharringtonine Analogs

Creator:: Zhang, Xiaojie
Abstract:: Substituted phenols are important substructures for pharmaceuticals, agrochemicals, natural products and biological probe molecules. The properties of phenolic molecules are substantially influenced by the substitution patterns of the phenolic ring. The chemical synthesis of phenols with various substitution patterns is an enduring challenge and multiple strategies have emerged. However, some...
Resource Type:: Dissertation

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:: : ______________________________________________________ Christopher M. Beaudry Aminal radical intermediates were generated by the method of

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:: transient chiral carbenoid reagents CHYMX (Y = heteroatom, X = nucleofuge, M = electrofuge). In the first

New, complex group 13 borates : synthesis, structures, and properties

Creator:: Chang, Ki-Seog
Resource Type:: Dissertation
Full Text:: , Prof. James H. Kruger, Prof. Michael M. Lemer, Prof. Kevin P. Gable, Prof. Kelly K. Falkner, and Prof

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

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:: me. I wish to thank my committee members Dr. Kevin Gable, Dr. Sandra Loesgen, Dr. Christopher

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:: ). SO2BT (a) (Me2Si)2NM (b) cC6H11CHO Reaction Solvent E:Z (23) M Toluene 50:50 54:46 54:46 Et2O 49:51

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:: ‐atom enrichment was clearly evident in mass (i.e., m/z (M + H)+ = 357 for [13C]2‐1), IR, and NMR

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:: -carboxamide was prepared in 83% yield from m-anisic acid via a sequence of transformations comprising

Total synthesis of phorboxazole A

Creator:: Lee, Tae Hee
Abstract:: The total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, is described. Both a palladium(II)-mediated and a palladium(II)-catalyzed intramolecular alkoxycarbonylation were used as key steps for the preparation of the two cis-2,6-disubstituted tetrahydropyran rings (C22-C26 and C11-C15) of phorboxazole A. The synthesis used a convergent approach involving...
Resource Type:: Dissertation
Full Text:: phorboxazole A inhibited growth of colon tumor cells HCT-116 (GI50 4.36 x 10-10 M) and HT29 (GI50 3.31 x 10

ScholarsArchive@OSU

Regioselective Synthesis of Substituted Phenols, Benzenes, Benzofuranones and Benzofurans and Synthesis of Homoharringtonine Analogs

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

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

New, complex group 13 borates : synthesis, structures, and properties

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

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

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

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

Total synthesis of phorboxazole A

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