Open Access. Powered by Scholars. Published by Universities.®
Physical Sciences and Mathematics Commons™
Open Access. Powered by Scholars. Published by Universities.®
Articles 1 - 2 of 2
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
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.
C-2/C-3 Annulation And C-2 Alkylation Of Indoles With 2-Alkoxycyclopropanoate Esters., Barbora Bajtos, Ming Yu, Hongda Zhao, Brian L Pagenkopf
C-2/C-3 Annulation And C-2 Alkylation Of Indoles With 2-Alkoxycyclopropanoate Esters., Barbora Bajtos, Ming Yu, Hongda Zhao, Brian L Pagenkopf
Chemistry Publications
The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.