De novo asymmetric synthesis of fridamycin E |
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Authors: | Chen Qian Mulzer Michael Shi Pei Beuning Penny J Coates Geoffrey W O'Doherty George A |
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Institution: | Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA. |
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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). |
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