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Synthesis 1992; 1992(8): 731-733
DOI: 10.1055/s-1992-26208
short paper
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2-Chloro-1-methoxymethylindole-3-carboxaldehyde: Introduction of Nucleophiles into the Indole 2-Position and an Approach to the Unusual TrpHis Fragment of Moroidin

Mark F. Comber* , Christopher J. Moody
  • *Department of Chemistry, Loughborough University of Technology, Loughborough, Leicestershire LE11 3TU, England
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Publication Date:
17 September 2002 (online)

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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.