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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 and Llona-Minguez, Sabin and Lang, Stuart and MacKay, Simon P. and Suckling, Colin J. and Sutcliffe, Oliver B. (2011) Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate : concise synthesis of alangiobussinine. Beilstein Journal of Organic Chemistry, 7. pp. 1407-1411. ISSN 1860-5397

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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.