Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A |
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Authors: | Hiromu Hattori Joel Roesslein Dr Patrick Caspers Dr Katja Zerbe Dr Hideki Miyatake‐Ondozabal Dr Daniel Ritz Dr Georg Rueedi Prof Dr Karl Gademann |
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Institution: | 1. Department Chemistry, University of Zurich, Zurich, Switzerland;2. Idorsia Pharmaceuticals Ltd, Allschwil, Switzerland |
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Abstract: | The macrocyclic antibiotic mangrolide A has been described to exhibit potent activity against a number of clinically important Gram‐negative pathogens. Reported is the first enantioselective total synthesis of mangrolide A and derivatives. Salient features of this synthesis include a highly convergent macrocycle preparation, stereoselective synthesis of the disaccharide moiety, and two β‐selective glycosylations. The synthesis of mangrolide A and its analogues enabled the re‐examination of its activity against bacterial pathogens, and only minimal activity was observed. |
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Keywords: | antibiotics carbohydrates glycosylation natural products total synthesis |
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