A concise,total synthesis and antibacterial evaluation of 2-hydroxy-1-(1H-indol-3-yl)-4-methylpentan-3-one |
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| Authors: | Son T. Nguyen Michelle M. Butler Laszlo Varady Norton P. Peet Terry L. Bowlin |
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| Affiliation: | 1. Microbiotix, Inc., One Innovation Dr., Worcester, MA 01605, USA;2. Rilas Technologies, Inc., 16 Walnut Hill Road, Newton, MA 02459, USA |
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| Abstract: | Treatment of racemic 2-hydroxy-3-(1H-indol-3yl)propionic acid methyl ester (5) with isopropyl magnesium chloride provided the title compound 1 and its isomer, 3-hydroxy-1-(indol-3-yl)-4-methylpentan-2-one (9). Both enantiomers (>96% ee) of each component were obtained via semi-preparative chiral supercritical fluid chromatography (SFC). In contrast to previous reports, these compounds, as well as their acetate derivatives, were not active or very weakly active against 16 bacterial strains, including Escherichia coli, Bacillus subtilis and Staphylococcus aureus. |
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