Virantmycin und Spiculoinsaure A – die intramolekulare Diels-Alder-Reaktionin in der Synthese komplexer Naturstoffe

By (author) Daniel Keck

Extent: 224 pages

Publisher: Logos Verlag Berlin

Subjects: Earth & Life Sciences

Series: Beiträge zur organischen Synthese

Series volume number: 4

Language: German

Paperback (Published)

(January 2007)

ISBN: 9783832514686

5.75 x 8.31 inches

Price: $61.00

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Synopsis
Contributing Authors

Die Diels-Alder-Reaktion ist eine der wichtigsten Methoden zur Darstellung von komplexen sechsgliedrigen Ringsystemen. Insbesondere die intramolekulare Variante dieses Reaktionsprinzips hat sich als eines der meistverwendeten Werkzeuge in der Synthese von Naturstoffen etabliert. Die beiden pharmakologisch relevanten Naturstoffe Virantmycin und Spiculoinsaure A sollten auf diese Art und Weise aufgebaut werden. Im Rahmen dieser Arbeit konnte die formale Totalsynthese des antiviral und antifungal wirksamen Naturstoffes Virantmycin durch Einsatz einer Variante der Appel-Reaktion sowie einer intramolekularen Aza-Diels-Alder-Reaktion als Schlusselreaktionen erreicht werden. Im weiteren Verlauf wurden Arbeiten zur Synthese des cytotoxischen marinen Naturstoffes Spiculoinsaure A durchgefuhrt. Dabei sollte ein fur die geplante intramolekulare Diels-AlderReaktion geeigneter linearer Vorlaufer dargestellt werden. Dazu wurde eine Reihe verschiedener Bausteine unter Verwendung und Optimierung diastereoselektiverAldolreaktionen und Reduktionen in hohen Ausbeuten und Selektivitaten synthetisiert, die auch in anderen Naturstoffsynthesen nutzbringend eingesetzt werden konnen. Zusatzlich wurde ein Screening verschiedener Methoden zur Verknupfung der Bausteine zum linearen Vorlaufer durchgefuhrt.

By (author) Daniel Keck

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