Total synthesis of desferrisalmycin B.
The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.
Dong
Li
L
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
Roosenberg
John M
JM
Miller
Marvin J
MJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D004187:Disaccharides / Q000138:chemical synthesis*; D005290:Ferric Compounds / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D017262:Siderophores / Q000138:chemical synthesis; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D004187:Disaccharides; D005290:Ferric Compounds; D017262:Siderophores; C471687:desferrisalmycin B