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ISBN 9783843933414

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978-3-8439-3341-4, Reihe Organische Chemie

Amelie Gutmann
Towards the Total Synthesis of Thailandepsin A: Application of Rhodium-Catalyzed Coupling of Allenes with Carboxylic Acids in Total Synthesis

249 Seiten, Dissertation Albert-Ludwigs-Universität Freiburg im Breisgau (2017), Softcover, A5

Zusammenfassung / Abstract

Due to the extraordinary potency as a HDCA inhibitor, the natural product thailandepsin A has attracted a lot of attention in the recent years. Besides its pharmaceutical activity, its structure containing a branched allylic ester aroused our interest. During the last five years an elegant hydrooxycarbonylation via Rhodium catalyzed coupling of allenes with carboxylic acids leading to branched allylic esters has been developed in our group. Inspired by these publications, this methodology was proposed to be a promising key step in the total synthesis of thailandepsin A. Furthermore, the allylic ester moiety is present in all members of the thailandepsin family, offering the opportunity to demonstrate the benefits of the stereoselective hydrooxycarbonylation.

The objective of the dissertation was to implement this atom economic regio- and stereoselective methodology in the reaction pathway towards the total synthesis of thailandepsin A. The desired and highly useful branched allylic esters were obtained in excellent yields and high diastereoselectivities. Thus, a completely new approach for the synthesis of thailandepsin A was created. Additionally, the developed route towards thailandepsin A should provide access to new derivatives and the syntheses of further members of the thailandepsin family.