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      Total Synthesis of vallartanone A

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      Lai, Leon_MSc_Total Synthesis of vallartanone A_October_2014 (ETD Version)1.pdf (2.880Mb)
      Date
      2014-11-12
      Author
      Lai, Leon Chun Kiu 1986-
      Type
      Thesis
      Degree Level
      Masters
      Metadata
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      Abstract
      The research presented herein describes the first enantioselective total syntheses of vallartanone A and its (8R) epimer both starting with propanoic acid and isobutyraldehyde. The key steps involved a proline-catalyzed intermolecular aldol reaction and a second aldol reaction that proceeded with kinetic resolution. It is concluded that the absolute configuration of vallartanone A should be revised to (3S,4S,8S).
      Degree
      Master of Science (M.Sc.)
      Department
      Chemistry
      Program
      Chemistry
      Committee
      Ward, Dale E; Dimmock, Jonathan R; Majewski, Marek
      Copyright Date
      October 2014
      URI
      http://hdl.handle.net/10388/12661
      Subject
      vallartanone, kinetic resolution, kinetic, resolution, aldol, total synthesis
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