Beilstein Journal of Organic Chemistry p. 1407 - 1411 (2011)
Update date:2022-08-11
Topics:
Baiget, Jessica
Llona-Minguez, Sabin
MacKay, Simon P.
Sutcliffe, Oliver B.
Lang, Stuart
Suckling, Colin J.
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.
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