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Synthese des Pyrrolizidin‐Alkaloides (±)‐Trachelanthamidin
Author(s) -
Horni Albert,
Hubáček Ivana,
Hesse Manfred
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770221
Subject(s) - chemistry , pyrrolizidine , nitromethane , pyrrolidine , alkaloid , diastereomer , pyrrolizidine alkaloid , derivative (finance) , stereochemistry , alcohol , hydrochloride , isoquinoline , organic chemistry , financial economics , economics
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 (NaBH 4 , 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.