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Physical Sciences and Mathematics Commons

Open Access. Powered by Scholars. Published by Universities.®

2009

Chemistry Publications

Isoquinolines

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Full-Text Articles in Physical Sciences and Mathematics

Synthesis Of Tetrahydroisoquinocarbazoles Via C-2 Alkylation Of Indoles With 2-Alkoxycyclopropanoate Esters., Barbora Bajtos, Brian L Pagenkopf Jun 2009

Synthesis Of Tetrahydroisoquinocarbazoles Via C-2 Alkylation Of Indoles With 2-Alkoxycyclopropanoate Esters., Barbora Bajtos, Brian L Pagenkopf

Chemistry Publications

A concise method for the synthesis of several tetrahydroisoquinocarbazole derivatives is reported, where the core is prepared in six steps from tryptophol in 51% overall yield. The pentacyclic analogs are constructed via a dipolar C-2 alkylation of a 3-substituted indole with a 2-alkoxycyclopropanoate ester and a SmBr(2)-HMPA mediated ketyl-alkene ring closure.