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Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A
Author(s) -
Hattori Hiromu,
Roesslein Joel,
Caspers Patrick,
Zerbe Katja,
MiyatakeOndozabal Hideki,
Ritz Daniel,
Rueedi Georg,
Gademann Karl
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201805770
Subject(s) - total synthesis , disaccharide , moiety , glycosylation , enantioselective synthesis , stereochemistry , chemistry , antibiotics , stereoselectivity , convergent synthesis , combinatorial chemistry , biochemistry , catalysis
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.