Work

De Novo Asymmetric Synthesis of Fridamycin E

Year: 2011

Type: article

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).

Source: Organic Letters

DOI: 10.1021/ol203041b

Authors: Qian Chen, Michael Mulzer, Pei Shi, Penny J. Beuning, Geoffrey W. Coates, George A. O’Doherty

Institutions: Northeastern University, Cornell University

Language: Hebrew

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G3337828607, G4347360969, De Novo Synthesis of Oligosaccharides, De Novo Synthesis for MedChem on Sugars