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The total synthesis of (-)- and (+)-membrenone-C, and, The formal synthesis of cytostatin

Posted on:2005-10-03Degree:Ph.DType:Thesis
University:University of VirginiaCandidate:Ellis, Keith CrossmanFull Text:PDF
GTID:2451390008994700Subject:Chemistry
Abstract/Summary:PDF Full Text Request
The total syntheses of the marine natural products (−)- and (+)-membrenone-C are described. The polypropionate segment of the molecule is synthesized by non-racemic allenyl metal additions. Hydrosilylation chemistry is used to transform the alkynes in the fully elaborated carbon backbone into β-hydroxy ketones. Finally, the dihydropyranone rings are closed using titanium aldol chemistry.; The formal synthesis of the PP2A inhibitor cytostatin is discussed. One allenyl metal addition and two Noyori transfer hydrogenations are used to set the six stereocenters in the molecule. The critical hydrogenation of a propargyl alcohol is described.
Keywords/Search Tags:Synthesis
PDF Full Text Request
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