Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A. (18th July 2018)

• Record Type: Journal Article
• Authors: Hattori, Hiromu; Roesslein, Joel; Caspers, Patrick; Zerbe, Katja; Miyatake‐Ondozabal, Hideki; Ritz, Daniel; Rueedi, Georg; Gademann, Karl
• Is Part Of: Angewandte Chemie. Volume 130:Number 34(2018)
• Page Start: 11186
• Page End: 11190
• Publication Date: 2018-07-18
• Subjects: Antibiotika -- Glykosylierung -- Kohlenhydrate -- Naturstoffe -- Totalsynthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201805770
• Languages: English
• ISSNs: 0044-8249

Abstract

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.