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).

SUBMITTER: Chen Q 

PROVIDER: S-EPMC3476477 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature