A short synthesis of the endogenous plant metabolite 7-hydroxyoxindole-3-acetic acid (7-OH-OxIAA) using simultaneous C-H borylations
A short synthesis of the endogenous plant metabolite 7-hydroxyoxindole-3-acetic acid (7-OH-OxIAA) using simultaneous C-H borylations
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DOI：
10.1016/j.tetlet.2014.08.104
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发表时间：
2014-10-15
影响因子：
1.8
通讯作者：
Sperry, Jonathan
中科院分区：
文献类型：
--
作者：
Homer, Joshua A.;Sperry, Jonathan
Methyl indole-3-acetate undergoes two simultaneous iridium-catalysed borylations to deliver exclusively 2,7-diboronate, with the ligand 3,4,7,8-tetramethyl-1,10-phenanthroline (Me(4)Phen) pivotal in driving the diborylation to completion. Subsequent oxidation-hydrolysis of the diboronate provides methyl 7-hydroxyoxindole-3-acetate which upon hydrolysis of the ester delivers 7-OH-OxIAA, an antioxidant, endogenous metabolite of indole-3-acetic acid found in various types of corn. This route has an overall yield of 50%, involves a single chromatographic purification and is an efficient alternative to existing syntheses, made possible by executing simultaneous oxidations at the indole C2 and C7 sites. (C) 2014 Elsevier Ltd. All rights reserved.
