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

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...

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Published inBeilstein journal of organic chemistry Vol. 7; pp. 1407 - 1411
Main Authors Baiget, Jessica, Llona-Minguez, Sabin, Lang, Stuart, MacKay, Simon P, Suckling, Colin J, Sutcliffe, Oliver B
Format Journal Article
LanguageEnglish
Published 12.10.2011
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Summary: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 9 H -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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.164