Synthese des Pyrrolizidin-Alkaloides (±)-Trachelanthamidin |
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Authors: | Albert Horni Ivana Hub
ek Manfred Hesse |
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Institution: | Albert Horni,Ivana Hubá?ek,Manfred Hesse |
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Abstract: | Synthesis of the Pyrrolizidine Alkaloid (±)-Trachelanthamidine The important intermediate in the synthesis of the title compound 8 is the diastereoisomer mixture of ethyl 2-2-(1,3 dioxolan-2-yl)ethyl]-5-oxopyrrolidine-3-carboxylate ( 3a/3b ) which was prepared from nitromethane, acrylaldehyde, and diethyl fumarate (Scheme). Its reduction (NaBH4, t-BuOH, MeOH) gave exclusively the trans-alcohol 4a , which was converted to the protected pyrrolidine derivative 6 . The deprotection and reduction of 6 gave the pyrrolizidine alkaloid 8 , characterized as its hydrochloride. |
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