Phenol oxidation and biosynthesis. Part 26. Isonitriles in the synthesis of benzylisoquinoline derivatives

Anthony G M Barrett, Derek H R Barton, John R. Falck, Dionysios Papaioannou, David A. Widdowson

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Abstract

Lithiomethyl and toluene-4-sulphonyl(potassiomethyl)isonitriles have been applied in short high-yield homologations of O-benzylvanillin, O-benzylisovanillin, and veratraldehyde giving N-(2-arylethyl)-2-arylacetamides and subsequently isoquinoline derivatives. These experiments are relevant to the preparation of alkaloids including papaverine and reticuline.

Original languageEnglish (US)
Pages (from-to)652-661
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - Dec 1 1979

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ASJC Scopus subject areas

  • Chemistry(all)

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