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

Research output: Contribution to journalArticle

14 Citations (Scopus)

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 - 1979

Fingerprint

Benzylisoquinolines
Papaverine
Biosynthesis
Toluene
Phenol
Alkaloids
Derivatives
Oxidation
Experiments
reticuline
benzylvanillin
veratraldehyde
isoquinoline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Phenol oxidation and biosynthesis. Part 26. Isonitriles in the synthesis of benzylisoquinoline derivatives. / Barrett, Anthony G M; Barton, Derek H R; Falck, John R.; Papaioannou, Dionysios; Widdowson, David A.

In: Journal of the Chemical Society, Perkin Transactions 1, 1979, p. 652-661.

Research output: Contribution to journalArticle

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