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      Towards the synthesis of hyacinthacines

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      DELAWARALLY-THESIS.pdf (1.444Mb)
      Date
      2012-02-10
      Author
      Delawarally, Khalil
      Type
      Thesis
      Degree Level
      Masters
      Metadata
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      Abstract
      The organocatalytic aldol reaction of tropinone with benzaldehyde using (S)-5-pyrrolidin-2-yl-1H-tetrazole as organocatalyst is described and it results in the formation of the dehydrated aldol adduct in moderate selectivity. The organocatalytic aldol reaction of CS and C2V-symmetrical dioxanones is also demonstrated and in most cases CS-symmetrical dioxanones offer a better stereoselectivity. A new approach towards synthesis of hyacinthacine alkaloids: 2-epihyacinthacine A2, 3-epihyacinthacine A2 and their enantiomers is illustrated. The key step involves an organocatalytic aldol reaction of dioxanones where proline is used both as the catalyst and as the precursor for the aldehyde building block.
      Degree
      Master of Science (M.Sc.)
      Department
      Chemistry
      Program
      Chemistry
      Supervisor
      Majewski, Marek
      Committee
      Gravel, Michel; Dimmock, Jonathan
      Copyright Date
      November 2011
      URI
      http://hdl.handle.net/10388/ETD-2011-11-197
      Subject
      Organocatalytic aldol
      tropinone
      syn aldol
      hyacinthacines
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