Index Catalog // ScholarsArchive@OSU

Catalytic desymmetrization of D₂d̳-symmertic proprochiral tetrasubstituted biphenyl compounds: a novel approach to the synthesis of axially chiral C₂-symmetric molecules

Creator:: Gunderson, Jeremey Tyson
Abstract:: Many D2d-symmetric 2,2',6,6'-tetrasubstituted biphenyls are readily prepared via net oxidative dimerization of appropriate 1,3-disubstituted benzenes. Conversion of such proprochiral compounds to useful C2-symmetric chiral biphenyls requires formal replacement of two substituents on opposing aryl ring units with alternate groups. This under exploited desymmetrization tactic has been demonstrated for the generation...
Resource Type:: Masters Thesis
Full Text:: Abstract approved: Paul R. Blakemore Many D2d-symmetric 2,2',6,6'-tetrasubstituted biphenyls are

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

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

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

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:: expresses sincere appreciation to the following people: Prof. Paul R. Blakemore, for his outstanding

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

Sex and Survival: Reproduction and Anti-Microbial Defense in the Red-Sided Garter Snake (Thamnophis sirtalis parietalis)

Creator:: Blakemore, Leslie A.
Abstract:: The red-sided garter snakes (Thamnophis sirtalis parietalis) of Manitoba, Canada, have been extensively studied for decades with little investigation into their immune system. These animals live very close to the arctic circle and spend over half of the year underground brumating. The annual cycle of the red-sided garter snakes make...
Resource Type:: Masters Thesis
Full Text:: ABSTRACT OF THE THESIS OF Leslie Blakemore for the degree of Master of Science in Integrative Biology

The Deathscape of St. Paul: Historic Cemeteries as Cultural Landscapes

Creator:: Boulware, Brooke L.
Abstract:: A cultural landscape analysis of two historic cemeteries in St. Paul, Oregon demonstrates that the residents of this early community were unknowingly using grave markers to express their worldview and the identities that they felt were most important. Because of the historical and cultural development of this community as the...
Resource Type:: Masters Thesis
Full Text:: of St. Paul: Historic Cemeteries as Cultural Landscapes Abstract approved: David R

Bioprospecting the Chemical Diversity of Plant-associated Fungi

Creator:: González-Montiel, Gisela Abigail
Abstract:: Fungi have long been used for discovery of new chemical scaffolds. In the clinical setting, the fungal natural products penicillin, statins, and cyclosporine have revolutionized medicine to treat diseases and infections. In the environment, fungal natural products have been used as herbicides, fungicides, and insecticides to protect crops, livestock, and...
Resource Type:: Masters Thesis

Development of organocatalyzed, intramolecular heteroatom Michael addition and application towards alkaloid synthesis

Creator:: Carlson, Erik
Abstract:: Effective methods for the enantiopure formation of substituted piperidine rings are significantly important due to their presence in alkaloid products. A valuable method to form these ring systems would be via an intramolecular heteroatom Michael addition from the corresponding enone or enal. Described herein is a methodolgy that has been...
Resource Type:: Masters Thesis
Full Text:: extend my appreciation to my committee members, Prof. Paul R. Blakemore, Prof. Kevin P. Gable, Prof

ScholarsArchive@OSU

Catalytic desymmetrization of D₂d̳-symmertic proprochiral tetrasubstituted biphenyl compounds: a novel approach to the synthesis of axially chiral C₂-symmetric molecules

Total synthesis of sparteine alkaloids from a common tetraoxobispidine intermediate

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

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

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

Sex and Survival: Reproduction and Anti-Microbial Defense in the Red-Sided Garter Snake (Thamnophis sirtalis parietalis)

The Deathscape of St. Paul: Historic Cemeteries as Cultural Landscapes

Bioprospecting the Chemical Diversity of Plant-associated Fungi

Development of organocatalyzed, intramolecular heteroatom Michael addition and application towards alkaloid synthesis

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