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Graduation date: 1996

PART I. Asymmetric syntheses of both natural (+)- and nonnatural (-)- byssochlamic acid via a [2+2] photoaddition-cycloreversion strategy are described. X-ray crystallographic analysis of the cyclohexylamine salt 99 showed that the structure of the monomethyl ester 100 from esterase hydrolysis of 44 was originally misassigned as 56. The enantiomeric relationship of the two diolides 106 and 70 permitted syntheses of nonnatural byssochlamic acid (-)-3 and natural byssochiamic acid (+)-3 from enantiopure alcohol (+)-64 and from its enantiomer (-)-110, respectively. Through the use of (��)-103 to reach both enantiomers of byssochlamic acid (3) and subsequent epimerization of the npropyl chain, it was proved that the cis configuration of the two alkyl substituents is strongly preferred in the natural product. PART II. An asymmetric approach towards the nootropic agent huperzine A is described. Formation of cyclobutane 122 with the desired stereochemistry was accomplished using intramolecular [2+2] photoaddition of the enantiopure enone 121. Attempts to prepare the methoxypyridine system via an azadiene Diels- Alder reaction were unsuccessful. However, intramolecular Michael addition of 181 produced silyl ether 182 which was converted into the pyridone 187 by treatment with hydrogen fluoride followed by selenoxide elimination. Attempts to effect the key sigmatropic rearrangement of ketone 197 into a direct precursor of huperzine A were unsuccessful. / Graduation date: 2001

Thesis (M.S.)--University of Akron, Dept. of Biomedical Engineering, 2008. / "August, 2008." Title from electronic thesis title page (viewed 12/9/2009) Advisor, Stephanie T. Lopina; Committee members, Amy Milsted, Daniel B. Sheffer, Daniel Ely; Department Chair, Daniel B. Sheffer; Dean of the College, George K. Haritos; Dean of the Graduate School, George R. Newkome. Includes bibliographical references.

Thesis (Ph. D.)--UCLA, 2008. / Vita. Includes bibliographical references (leaves 276-312).

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The behavioural and electrophysiological consequences of two newly developed aniracetam analogues were investigated in male Long-Evans rats. Results indicate that an intraperitoneal (i.p.) injection of LD38.2 significantly improved retention in a two odour olfactory discrimination task. However, three different dosages of LN1 did not facilitate memory in the task. In rats with chronically implanted electrodes, both compounds rapidly crossed the blood brain barrier (BBB) after an i.p. injection and influenced several parameters of the field excitatory postsynaptic potential (EPSP) in the CA1 and dentate gyrus regions of the hippocampus. The enhancement of the field EPSP following LD38.2 administration may be related to the drug's ability to facilitate memory in the olfactory discrimination task. Compounds, like LD38.2, that enhance both hippocampal transmission and performance in learning/memory tasks in laboratory rodents may have implications for the treatment of clinical memory disorders.

No description available.