Synthesis of tetrahydroisoquinocarbazoles via C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.
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.
Bajtos
Barbora
B
Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada.
Pagenkopf
Brian L
BL
D000478:Alkylation; D000586:Amination; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D007211:Indoles / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D002227:Carbazoles; D003521:Cyclopropanes; D004952:Esters; D007211:Indoles; D007546:Isoquinolines; C073517:RS 2135