title: De novo asymmetric synthesis of fridamycin E.
abstract: A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a β-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 μM).
authors: Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA.
authors: Qian
authors: Q
authors: Chen
authors: Michael
authors: M
authors: Mulzer
authors: Pei
authors: P
authors: Shi
authors: Penny J
authors: PJ
authors: Beuning
authors: Geoffrey W
authors: GW
authors: Coates
authors: George A
authors: GA
authors: O'Doherty
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D004926:Escherichia coli / Q000187:drug effects*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000880:Anthraquinones; D000900:Anti-Bacterial Agents; C569983:fridamycin E