Tetrahedron Letters p. 3905 - 3908 (1994)
Update date:2022-08-04
Topics:
Jefford, Charles W.
Thornton, Steven R.
Sienkiewicz, Krzysztof
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.
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