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      • HARVEST
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      The thiopyran route to polypropionates : sequential enantiotopic group selective enolization of meso 1,9-diketones

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      Date
      2007
      Author
      Gillis, Harold Martin
      Type
      Thesis
      Degree Level
      Doctoral
      Metadata
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      Abstract
      Meso 1,9-diketones (six to seven stereocenters)are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde. Enantioselective enolizations of these diketones with the lithium amide from (R,R)-bis(1-phenylethyl)amine occur with simultaneous kinetic resolution to give the mono-TMS enol ethers in >90% yields based on recovered starting material (BORSM) and >90% ee. The developed methodology was applied in synthetic studies towards the asymmetric synthesis of denticulatin A.
      Degree
      Doctor of Philosophy (Ph.D.)
      Department
      Chemistry
      Program
      Chemistry
      Supervisor
      Ward, Dale E.
      Committee
      Attah-Poku, Sam; Palmer, David; Majewski, Marek; Kerr, Michael A.; Baranski, Andrzej S.
      Copyright Date
      2007
      URI
      http://hdl.handle.net/10388/etd-09242007-122538
      Subject
      desymmetrization
      denticulatin
      chiral lithium amide
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      • Graduate Theses and Dissertations
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