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Synthese Alpha-Allenischer Isocarbacyclin-Derivate Und Vanadium(v)-Katalysierte Stereospezifische Umlagerung Von Allylalkoholen

Synthese Alpha-Allenischer Isocarbacyclin-Derivate Und Vanadium(v)-Katalysierte Stereospezifische Umlagerung Von Allylalkoholen

          
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About the Book

Prostaglandine sind biologisch wichtige und vielseitige Naturstoffe. Sowohl Prostaglandine selbst als auch zahlreiche ihrer Derivate wurden bereits erfolgreich als Arzneimittel eingesetzt. In einigen Fallen konnte durch das Einfuhren einer Allenfunktionalitat eine Verbesserung der medizinischen Eigenschaften erreicht werden. Isocarbacyclin, ein Derivat des naturlich vorkommenden Prostacyclins, wurde entwickelt, um die Stabilitat unter physiologischen Bedingungen zu erhohen. Ziel der vorliegenden Arbeit war die Zusammenfuhrung dieser beiden Ansatze, also die Synthese allenischer Isocarbacyclin-Derivate. Eine stereoselektive Totalsynthese dieser neuen pharmakologisch interessanten Verbindungen wird vorgestellt. Angeregt von einem Teilschritt dieser Synthese wurde im zweiten Teil dieser Arbeit die stereospezifische Umlagerung von Allylalkoholen untersucht. Die 1,3-Isomerisierung von Allylalkoholen ist von betrachtlichem synthetischem Interesse, da ein Regioisomer leichter zuganglich sein kann als das andere. In dieser Arbeit wurde gezeigt, dass solche Umlagerungen mit einem Vanadium(V)-Katalysator bei Raumtemperatur in guten Ausbeuten moglich sind. Als Substrate wurden Allylalkohole eingesetzt, deren Regioisomer eine konjugierte Doppelbindung enthalt. Dies wurde durch die Einfuhrung von Phenyl- oder Alkinylsubstituenten erreicht. Da bisher nur wenige Untersuchungen zur Stereospezifitat dieser Reaktion existieren, wurde der Chiralitatstransfer verstarkt untersucht. Es konnte gezeigt werden, dass die Umlagerung in der Regel ohne nennenswerte Einbussen an chiraler Information verlauft.


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Product Details
  • ISBN-13: 9783832521851
  • Publisher: Logos Verlag Berlin
  • Binding: Paperback
  • Language: German
  • Returnable: N
  • Spine Width: 0 mm
  • Width: 145 mm
  • ISBN-10: 3832521852
  • Publisher Date: 22 Apr 2009
  • Height: 210 mm
  • No of Pages: 142
  • Series Title: German
  • Weight: 700 gr

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