Development of a focused chemical library: synthesis of novel bioactive hymenialdisine derivatives

Hanns Martin Kaiser

doi:10.18453/rosdok_id00000389

Hanns Martin Kaiser

Development of a focused chemical library: synthesis of novel bioactive hymenialdisine derivatives

Universität Rostock, 2008

https://doi.org/10.18453/rosdok_id00000389

Abstract: This dissertation deals with the synthesis of novel bioactive derivatives of the natural occurring hymenialdisine. As a part of this project, a solvent-free, efficient, and easy to handle diversification strategy for annulated hymenialdisine-type bisindoles was developed. A C-C bond-formation reaction on activated silica under mild reaction conditions starting from aziridines, epoxides or hydroxyl compounds is the key technology. The versatility of different aziridines as key building blocks was demonstrated with H-, O-, and N-nucleophiles in a diversity oriented synthesis to build up a focused chemical library. Furthermore, novel transition metal mediated introduction and transformation of functional-groups for potential application in the synthesis of novel drug candidates were developed.

doctoral thesis free access

title:

Development of a focused chemical library: synthesis of novel bioactive hymenialdisine derivatives

contributing persons:

Hanns Martin Kaiser[VerfasserIn]
	137102895
Matthias Beller , Prof. Dr.[AkademischeR BetreuerIn]
Armin Börner , Prof. Dr.[AkademischeR BetreuerIn]
Frank Glorius , Prof. Dr.[AkademischeR BetreuerIn]

contributing corporate bodies:

Universität Rostock, Mathematisch-Naturwissenschaftliche Fakultät[Grad-verleihende Institution]
	2147083-2

abstract:

This dissertation deals with the synthesis of novel bioactive derivatives of the natural occurring hymenialdisine. As a part of this project, a solvent-free, efficient, and easy to handle diversification strategy for annulated hymenialdisine-type bisindoles was developed. A C-C bond-formation reaction on activated silica under mild reaction conditions starting from aziridines, epoxides or hydroxyl compounds is the key technology. The versatility of different aziridines as key building blocks was demonstrated with H-, O-, and N-nucleophiles in a diversity oriented synthesis to build up a focused chemical library. Furthermore, novel transition metal mediated introduction and transformation of functional-groups for potential application in the synthesis of novel drug candidates were developed. [English]

Die vorliegende Dissertation beschäftigt sich mit der Synthese von neuartigen biologisch-aktiven Derivaten des Naturstoffes Hymenialdisin. Dafür wurde eine lösungsmittelfreie, effiziente und einfach zu handhabende Diversifizierungsstrategie für die Synthese von Hymenialdisin-artigen Bisindolen entwickelt. Durch den Aufbau von C-C Bindungen auf aktiviertem Kieselgel unter milden Reaktionsbedingungen wurden die Zielprodukte ausgehend von Aziridinen, Epoxiden oder Alkoholen erhalten. Der flexible Einsatz verschiedener Aziridine als Schlüsselbausteine konnte durch Umsetzungen mit H-, O-, und N-Nukleophilen beim Aufbau einer fokussierten Substanzbibliothek gezeigt werden. Ein zweiter Schwerpunkt der Arbeit lag in der Entwicklung neuer Übergangsmetall-vermittelter Reaktionen für die Einführung und Transformation von funktionellen Gruppen für deren potentielle Anwendung in der Synthese biologisch aktiven Verbindungen [German]

document type:

doctoral thesis

institution:

Faculty of Mathematics and Natural Sciences

language:

English

subject class (DDC):

540 Chemistry & allied sciences

publication /
production:

Rostock: Universität Rostock

2008

identifiers: