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  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • A Diels-Alder approach to biaryl synthesis

    Creator:
    Ashburn, Bradley O.
    Abstract:
    An expedient approach to the synthesis of a wide range of highly programmable biaryl templates has been accomplished. Utilizing the Diels-Alder [4+2] cycloaddition, a wide range of tri- and tetra-ortho-substituted biaryls have been synthesized in only three to four steps from commercially available materials. We have successfully synthesized entire classes...
    Resource Type:
    Dissertation
    Full Text:
    . Paul R. Blakemore, Prof. Kerry L. McPhail, and Prof. William W. Warren for their guidance. I want to

  • Studies toward the total synthesis of (+)-providencin

    Creator:
    Jana, Somnath
    Abstract:
    Studies toward the total synthesis of (+)-providencin (1), a highly oxygenated cembranoid dipterpene with a unique bicyclo[12.2.0]hexadecane skeleton and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediates 320 and 332 which contain all of the carbon atoms of 1. In a first generation approach...
    Resource Type:
    Dissertation
    Full Text:
    , Professor Rich G. Carter, Professor Paul R. Blakemore, Professor Kevin P. Gable, Professor Janet Tate and

  • 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