154221-70-2Relevant academic research and scientific papers
An Enantiospecific Entry to Indolizidines by Intramolecular Acylation of N-Pyrrole Esters
Jefford, Charles W.,Thornton, Steven R.,Sienkiewicz, Krzysztof
, p. 3905 - 3908 (1994)
L-Glutamic diethyl ester hydrochloride was converted to its pyrrole derivative 22 by condensation with 2,5-dimethoxytetrahydrofuran in water.Cyclization of 22 with BBr3 afforded (5S)-5,6-dihydro-5-etoxycarbonyl-8(7H)-indolizinone (23).Catalytic hydrogenation of 23 over Pd/C in acetic acid gave exclusively (5S,9R)-5-ethoxycarbonylindolizidine in an overall yield of 41percent, whereas hydrogenation over Rh/Al2O3 in ethanol gave predominantly (5S,8S,9S)-5-ethoxycarbonyl-8-hydroxyindolizidine in 48.5percent overall yield.
Efficient Asymmetric Synthesis of Indolizidine Building Blocks
Bond, Timothy J.,Jenkins, Robert,Ridley, Andrew C.,Taylor, Paul C.
, p. 2241 - 2242 (2007/10/02)
Intramolecular Friedel-Crafts acylation of a pyrrole derived from L-glutamic acid, followed by a highly selective hydrogenation, leads to either of the optically pure indolizidine alkaloid precursors 6 or 7, depending on the catalyst.
