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Zugang zu Agrar- & Pharmawirkstoffen durch organische Synthese

Design und Synthese von Spinosynanaloga und Hsp47-Inhibitoren sowie enantioselektive Totalsynthese des Naturstoffes Linoxepin

Access to agricultural and pharmaceutical active ingredients by organic synthesis

Design and Synthesis of Spinosyn analogues and Hsp47 inhibitors as well as enantioselective total synthesis of the natural product Linoxepin

by Simon Biller
Doctoral thesis
Date of Examination:2015-06-10
Date of issue:2015-07-30
Advisor:Prof. Dr. Dr. h.c. Lutz Tietze
Referee:Prof. Dr. Dr. Lutz Tietze
Referee:Prof. Dr. Daniel Werz
Referee:Dr. Alexander Breder
Referee:Prof. Dr. Hartmut Laatsch
Referee:Prof. Dr. Sven Schneider
Referee:Prof. Dr. Ulf Diederichsen
crossref-logoPersistent Address: http://dx.doi.org/10.53846/goediss-5208

 

 

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Abstract

English

This thesis contains the design of new spinosyn analogues via two subsequent heck reactions as well as the modification of a beta-selective glycoslylation method and the synthesis of six new potential Hsp47 inhibitors based on recent results. In addition, an enantioselective synthesis of the lignan linoxepin in eleven steps with the highest overall yield so far was accomplished. Key steps are a domino carbopalladation-Heck reaction, an asymmetric hydroboration and an oxidative lactonization.
Keywords: organic synthesis; Spinosyn; Linoxepin; Hsp47 inhibitors

Other Languages

Diese Arbeit beinhaltet die Modellierung von neuartigen Spinosynanaloga über zwei aufeinanderfolgende Heck-Reaktionen und die Modifizierung einer beta-selektiven Glycosylierungsmethode sowie die Synthese von sechs neuen potentiellen Hsp47-Inhibitoren, die auf neuen Forschungsergebnissen basieren. Darüber hinaus wird ein enantioselektiver Zugang zu dem Lignan Linoxepin in elf Stufen mit der höchsten bisher erreichten Gesamtausbeute vorgestellt. Als Schlüsselschritte dienen hier eine Domino-Carbopalladierung-Heck-Reaktion, eine asymmetrische Hydroborierung und eine oxidative Lactonisierung.
Schlagwörter: Organische Synthese; Spinosyn; Linoxepin; Hsp47 inhibitors
 

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