SYNTHETIC STUDIES ON INDOLE ALKALOIDS .8. SYNTHESIS AND REACTIVITY OFASYMMETRIC 2-INDOLYL-4-METHYLENEPIPERIDINES

Authors
MIGUEL D DIEZ A BLACHE Y LUQUE J OROZCO M REMUSON R GELASMIALHE Y RUBIRALTA M
Citation
D. Miguel et al., SYNTHETIC STUDIES ON INDOLE ALKALOIDS .8. SYNTHESIS AND REACTIVITY OFASYMMETRIC 2-INDOLYL-4-METHYLENEPIPERIDINES, Tetrahedron, 51(27), 1995, pp. 7527-7546
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
27
Year of publication
1995
Pages
7527 - 7546
Database
ISI
SICI code
0040-4020(1995)51:27<7527:SSOIA.>2.0.ZU;2-A
Abstract
The synthesis of asymmetric 2-indolyl-4-methylenepiperidines 8-11 and 14-15 by condensation of an aminoallylsilane with an indole carbaldehy de, followed by intramolecular cyclization of the intermediate, is des cribed. The reactivity of N-(2-hydroxyethyl)indolylpiperidines 9 and 1 4 with K(t)BuO to give indolo[2,3-a]quinolizidines is studied. Some un expected results are obtained due to the influence of the alpha-phenyl ring.