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

被引：12
|
作者：
Nguyen, Son T. [1 ]
Butler, Michelle M. [1 ]
Varady, Laszlo [2 ]
Peet, Norton P. [1 ]
Bowlin, Terry L. [1 ]
机构：
[1] Microbiotix Inc, Worcester, MA 01605 USA
[2] Rilas Technol Inc, Newton, MA 02459 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 19期
关键词：
Antibiotic; Xenorhabdus; Nematode; Acyloin natural products; XENORHABDUS-NEMATOPHILUS; BACTERIA XENORHABDUS; SORANGIUM-CELLULOSUM; INDOLE; BIOSYNTHESIS; ANTIBIOTICS;
D O I：
10.1016/j.bmcl.2010.08.003
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5739 / 5742
页数：4
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