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Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A


Hattori, Hiromu; Roesslein, Joel; Caspers, Patrick; Zerbe, Katja; Miyatake-Ondozabal, Hideki; Ritz, Daniel; Rueedi, Georg; Gademann, Karl (2018). Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A. Angewandte Chemie Internationale Edition, 57(34):11020-11024.

Abstract

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 b-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.

Abstract

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 b-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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis
Language:English
Date:2018
Deposited On:21 Nov 2018 17:17
Last Modified:23 Nov 2018 07:10
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/anie.201805770

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