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Syntheses of inositol natural products through asymmetric phosphorylation

Posted on:2011-02-27Degree:Ph.DType:Thesis
University:Yale UniversityCandidate:Rodrigo, Christina M. LongoFull Text:PDF
GTID:2441390002953478Subject:Chemistry
Abstract/Summary:
Chapter 1: Examples of organocatalytic asymmetric and regioselective non-acyl group transfers to alcohols are reviewed.;Chapter 2: The asymmetric syntheses of L,L- and L,D-di-myo-inositol-1,1'-phosphate is described. Each diastereomer was independently synthesized by the reaction of a chiral nucleophilic peptide catalyst with an inositol-containing chiral phosphoryl chloride to yield the desired diastereomer in each series. Both isomers were shown to exhibit thermoprotective activity of an enzyme at elevated temperature.;Chapter 3: Approaches towards the asymmetric synthesis of a glycosylphosphatidylinositol are discussed. These novel approaches utilize asymmetric phosphorylation to access the inositol portion.
Keywords/Search Tags:Asymmetric
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