Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: concise synthesis of alangiobussinine

Jessica Baiget, Sabin Llona-Minguez, Stuart Lang, Simon P. MacKay, Colin J. Suckling, Oliver B. Sutcliffe

Research output: Contribution to journalLetter

11 Citations (Scopus)

Abstract

The carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet–Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to β-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1-carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.
Original languageEnglish
Pages (from-to)1407-1411
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume7
Early online date12 Oct 2010
DOIs
Publication statusPublished - 12 Oct 2011

Keywords

  • manganese dioxide
  • one-pot synthesis
  • mediated
  • methyl 9H-pyrido[3,4-b]indole-1-carboxylate
  • alangiobussinine
  • alkaloid synthesis
  • tandem reaction
  • oxidation
  • heterocycle
  • carboline

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