Synthesis of Tetrahydroisoquinocarbazoles via C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters | Zendy

Barbora Bajtos | Zendy; Brian L. Pagenkopf | Zendy

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Synthesis of Tetrahydroisoquinocarbazoles via C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters

Author(s) -

Barbora Bajtos,

Brian L. Pagenkopf

Publication year - 2009

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol900937f

Subject(s) - chemistry , alkylation , alkene , yield (engineering) , ketyl , ring (chemistry) , indole test , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , radical , materials science , metallurgy

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.

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