113774-86-0Relevant academic research and scientific papers
Synthesis and conformational study of indolo[2,3-a]-quinolizidine-3-ethan-1'-ols: Intermediates for the synthesis of deplancheine and flavopereirine
Lounasmaa, Mauri,Karinen, Kimmo,Tolvanen, Arto
, p. 1397 - 1404 (2007/10/03)
The synthesis and stereostructures of all four indolo[2,3-a]-quinolizidine-3-ethan-1'-ols are described. The two alcohols with an axial side chain exist principally in the conformation where the C/D ring junction is trans, which is favoured by an intramolecular hydrogen bond between the hydroxyl group and the Nb-atom. Dehydration of the four alcohols with P2O5 in each case led to a mixture consisting of E-deplancheine and Z-deplancheine. The three side products were two 3-vinyl isomers, one of which can be converted to deplancheine via double bond isomerization, and 3-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine, which is a precursor of flavopereirine.
