Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 11, Pages 2884-2888Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800169
Keywords
amino acids; antibiotics; glycosylation; gold; natural products
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Funding
- National Natural Science Foundation of China [21372252, 21432012, 21621002]
- Strategic Priority Research Program of CAS [XDB20020000]
- K. C. Wong Education Foundation
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The proposed diastereoisomers (1a-d) together with their C8'-epimers (1e-h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereo-divergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3' in amipurimycin should be of opposite configuration.
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