Synthetic studies on indole alkaloids VIII. Synthesis and reactivity of asymmetric 2-indolyl-4-methylenepiperidines

Article abstract of DOI:10.1016/0040-4020(95)00376-J

The synthesis of asymmetric 2-indolyl-4-methylenepiperidines 8-11 and 14-15 by condensation of an aminoallylsilane with an indole carbaldehyde, followed by intramolecular cyclization of the intermediate, is described. The reactivity of N-(2-hydroxyethyl)indolylpiperidines 9 and 14 with K(t)BuO to give indolo[2,3-a]quinolizidines is studied. Some unexpected results are obtained due to the influence of the α-phenyl ring.