2-Chloro-1-methoxymethylindole-3-carboxaldehyde: Introduction of Nucleophiles into the Indole 2-Position and an Approach to the Unusual TrpHis Fragment of Moroidin

Abstract

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.