25834-22-4

Upstream product

• 1322763-70-1 (R)-2,4-dimethyl-pent-3-yl 2-[(1-hydroxymethyl)-1H-indol-3-yl]propionate 
• 1322763-71-2 (R)-2,4-dimethyl-pent-3-yl 2-(1H-indol-3-yl)propionate 
• 1322763-54-1 (R)-2,4-dimethyl-pent-3-yl 2-[1-methoxymethyl-1H-indol-3-yl]propionate 
• 40899-68-1 1-(methoxymethyl)-1H-indole 
• 2597-26-4 2-(1H-Indol-3-yl)-propionic acid 

Relevant academic research and scientific papers

Catalytic enantioselective C-H functionalization of indoles with α-diazopropionates using chiral dirhodium(II) carboxylates: Asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A

An enantioselective C-H functionalization of N-methoxymethyl (MOM)-protected 2,3-unsubstituted indoles with α-diazopropionates has been effected via catalysis by dirhodium(II) tetrakis[N-phthaloyl-(S)- triethylalaninate], Rh2((S)-PTTEA)4, providing α-methyl-3-indolylacetates in high yields and with enantioselectivities of up to 86% ee. The effectiveness of this protocol was demonstrated by the first catalytic asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A, a potent plant-growth inhibitor. Furthermore, the Fujioka protocol using a combination of TMSOTf and 2,2′-bipyridyl was shown to be superior for the removal of the N-MOM group.

Synthesis of Acremoauxin A, a New Plant Growth Regulator Produced by Acremonium roseum I 4267

Acremoauxin A, a new fungal auxin derivative produced by A. roseum I 4267, was synthesized from indole, lactic acid, and D-mannitol. (+)-2-(3-Indolyl)propionic acid was prepared from its synthetic racemate by biological resolution using the acremoauxin-producing fungus.The synthetically confirmed structure of acremoauxin A was 1-O--D-arabitol (1).