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

9 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.
LanguageEnglish
Pages1407-1411
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume7
Early online date12 Oct 2010
DOIs
Publication statusPublished - 12 Oct 2011

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Carbolines
Alcohols
Aromatization
Cyclization
Oxidation
manganese dioxide
harman

Keywords

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

Cite this

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title = "Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: concise synthesis of alangiobussinine",
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.",
keywords = "manganese dioxide , one-pot synthesis , mediated , methyl 9H-pyrido[3,4-b]indole-1-carboxylate, alangiobussinine, alkaloid synthesis, tandem reaction , oxidation, heterocycle, carboline",
author = "Jessica Baiget and Sabin Llona-Minguez and Stuart Lang and MacKay, {Simon P.} and Suckling, {Colin J.} and Sutcliffe, {Oliver B.}",
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language = "English",
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Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate : concise synthesis of alangiobussinine. / Baiget, Jessica; Llona-Minguez, Sabin; Lang, Stuart; MacKay, Simon P.; Suckling, Colin J.; Sutcliffe, Oliver B.

In: Beilstein Journal of Organic Chemistry, Vol. 7, 12.10.2011, p. 1407-1411.

Research output: Contribution to journalLetter

TY - JOUR

T1 - Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate

T2 - Beilstein Journal of Organic Chemistry

AU - Baiget, Jessica

AU - Llona-Minguez, Sabin

AU - Lang, Stuart

AU - MacKay, Simon P.

AU - Suckling, Colin J.

AU - Sutcliffe, Oliver B.

PY - 2011/10/12

Y1 - 2011/10/12

N2 - 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.

AB - 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.

KW - manganese dioxide

KW - one-pot synthesis

KW - mediated

KW - methyl 9H-pyrido[3,4-b]indole-1-carboxylate

KW - alangiobussinine

KW - alkaloid synthesis

KW - tandem reaction

KW - oxidation

KW - heterocycle

KW - carboline

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U2 - 10.3762/bjoc.7.164

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