A concise, total synthesis and antibacterial evaluation of 2-hydroxy-1-(1H-indol-3-yl)-4-methylpentan-3-one

作者：Nguyen Son T^*; Butler Michelle M; Varady Laszlo; Peet Norton P; Bowlin Terry L

来源：Bioorganic & Medicinal Chemistry Letters, 2010, 20(19): 5739-5742.

DOI：10.1016/j.bmcl.2010.08.003

• Antibiotic
• Xenorhabdus
• Nematode
• Acyloin natural products

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.

• 出版日期2010-10-1