2-Chloro-1-methoxymethylindole-3-carboxaldehyde: Introduction of nucleophiles into the indole 2-position and an approach to the unusual TrpHis fragment of moroidin

Article abstract of DOI:10.1055/s-1992-26208

2-Chloro-1-methoxymethylindole-3-carboxaldehyde (3) is an excellent substrate for a range of nitrogen nucleophiles and gives 2-substituted indoles. Use of a histidine based nucleophile results in the formation of the N-(2-indolyl)imidazole (11), a precursor for the unusually substituted tryptophan residue of the bicyclic octapeptide moroidin.