ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of the Pyrrolizidine Alkaloid (±)-TrachelanthamidineThe 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770221