Total Synthesis of Farnesyl Lipid I/II Analogs and Contributions to the Total Synthesis of Vancoresmycin

Abstract

Rapidly occurring bacterial resistance against approved medication is steadily increasing and represents an enormous threat for the human health in all parts of the world. Based on the burden of antibiotic resistance and its impact, this work is dedicated to antibiotic research. The present work is divided into two parts, which both focus on the fight against pathogenic bacteria. Spotlight of part one is the total synthesis of farnesyl lipid I/II analogs, which represent key building blocks in the bacterial cell wall biosynthesis and being therefore essential targets of many common antibiotics. The second part of this thesis addresses the synthesis towards vancoresmycin, which is characterized by a densely functionalized tetramic acid connected to a large polyketide chain bearing a plethora of stereogenic centers and also a carbohydrate moiety. In addition to the intriguing structure and the so far only proposed stereogenic centers, several potent antibiotic activities of vancoresmycin were determined against pathogenic bacteria.