Untersuchungen zur enantioselektiven Totalsynthese von Parnafungin C

Studies towards the Enantioselective Total Synthesis of Parnafungin C

by Sven Heidemann
Doctoral thesis
Date of Examination:2016-08-04
Date of issue:2016-10-10
Advisor:Prof. Dr. Dr. h.c. Lutz Tietze
Referee:Prof. Dr. Dr. H.c. Lutz Tietze
Referee:Prof. Dr. Ulf Diederichsen
Persistent Address: http://dx.doi.org/10.53846/goediss-5881

 

 

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Abstract

English

Within this thesis, two fragments of the natural product Parnafungin C, a highly functionalized chiral chromane with the correct absolute and relative configuration of all stereogenic centers as well as a biaryl system comprising all required substituents for the formation of the unique isoxazolidinone-moiety, were synthesized. Key steps are an enantioselective Wacker oxidation or a Domino-Wacker/carbonylation/methoxylation reaction, a Sharpless asymmetric dihydroxylation reaction and a Suzuki-Miyaura cross coupling reaction.
Keywords: Parnafungin C; Enantioselective Total Synthesis; Wacker oxidation; Domino reaction; Suzuki-Miyaura cross coupling; Sharpless dihydroxylation
 
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