Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic MangrolideA

The macrocyclic antibiotic mangrolideA has been described to exhibit potent activity against a number of clinically important Gram-negative pathogens. Reported is the first enantioselective total synthesis of mangrolideA and derivatives. Salient features of this synthesis include a highly convergent...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 57; no. 34; pp. 11020 - 11024
Main Authors Hattori, Hiromu, Roesslein, Joel, Caspers, Patrick, Zerbe, Katja, Miyatake-Ondozabal, Hideki, Ritz, Daniel, Rueedi, Georg, Gademann, Karl
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 20.08.2018
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
carbohydrates
CATALYSIS
NATURAL-PRODUCTS
glycosylation
TRITYL TETRAKIS(PENTAFLUOROPHENYL)BORATE
CLOSTRIDIUM-DIFFICILE
FLUORIDE
STEREOSELECTIVE GLYCOSYLATION
natural products
CONSTRUCTION
total synthesis
antibiotics
GLYCOSIDATION
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Summary:The macrocyclic antibiotic mangrolideA has been described to exhibit potent activity against a number of clinically important Gram-negative pathogens. Reported is the first enantioselective total synthesis of mangrolideA and derivatives. Salient features of this synthesis include a highly convergent macrocycle preparation, stereoselective synthesis of the disaccharide moiety, and two -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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201805770