Two concise total syntheses of the wasabi phytoalexin methyl 1-methoxyindole-3-carboxylate

Two new syntheses of the phytoalexin methyl 1-methoxyindole-3-carboxylate (1) were developed that employ the same key intermediate. Methyl 2-(2-nitrophenyl)acrylate (2) was directly converted into phytoalexin 1 using modified Cadogan-Sundberg indole synthesis conditions with trimethyl phosphite. Acrylate 2 also underwent reductive cyclization with stannous chloride to give methyl 1-hydroxyindole-3-carboxylate (3), which was methylated to produce phytoalexin I. (C) 2013 Elsevier Ltd. All rights reserved.