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Studies towards the total synthesis of biological active gamma-butyrolactones

URN to cite this document: urn:nbn:de:bvb:355-opus-8287

Schall, Andreas (2008) Studies towards the total synthesis of biological active gamma-butyrolactones. PhD, Universität Regensburg

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Abstract (English)

The aim of this work was to seek for the first synthetic route towards Cynaropicrin and Ixerin Y, two prominent guaianolides with promising biological activity. Using asymmetric cyclopropanation, enzymatic resolution, Sakurai allylation and retro-aldol-lactonization afforded a very advanced intermediate in excellent selectivity, which was used as a starting point for different ring closing strategies including radical cyclization and ring closing metathesis. Further functionalization towards the different natural products was also shown. Beside this route, two small molecule libraries were synthesized, leading to interesting natural product like scaffolds and promissing Gcn5-inhibitors.

Translation of the abstract (German)

Das Ziel dieser Arbeit war die erste Totalsynthese der Naturstoffe Cynaropicrin und Ixerin Y zu entwickeln. Diese beiden bekannten Guaianolide zeigen dabei eine vielversprechende biologische Aktivität. Anwendung fand dabei eine asymmetrische Cyclopropanierung, enzymatische Racematspaltung, selektive Sakurai-allylierung und eine retro-Aldol-Laktonisierung, was in excellenter Selektivität zu einem bereits hoch substituierten Intermediat führte. Dieses diente als Ausgangspunkt für verschieden Ringschlußreaktionen, darunter sowohl radikalische Cylclisierungen als auch Ringschlußmetathese. Weitere Funktionalisierungen hinsichtlich der Naturstoffe konnte ebenfalls gezeigt werden. Darüber hinaus wurden zwei Substanzbibliotheken aufgebaut, die sowohl interessante Naturstoffgerüste, als auch vielversprechende Gcn5-Inhibitoren enthalten.

Item Type:	Thesis of the University of Regensburg (PhD)
Referee:	Oliver (Prof. Dr.) Reiser
Date of exam:	26 June 2007
Institutions:	Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Keywords:	Totalsynthese , Guaianolide , Guaianolidderivate , Naturstoff , Stereoselektive Synthese , , Total synthesis , guaianolides , guaianolide derivatives , natural products , stereoselective synthesis
Subjects:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Yes
Owner:	Universitätsbibliothek Regensburg
Deposited On:	27 Oct 2009 17:13
Last Modified:	29 Oct 2012 08:55
Item ID:	10678

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