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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Approaches to the Synthesis of Retronecine From Some Pyrrolidine Precursors

BW Clare, V Ferro, BW Skelton, RV Stick and AH White

Australian Journal of Chemistry 46(6) 805 - 824
Published: 1993

Abstract

Procedures are described for the attempted conversion of the pyrrolidine (2) into a bicyclic system that would ultimately lead to retronecine (3). The only molecule to be isolated from these attempts was the epimeric ketone (6), and AM1 and MM2 calculations were used to probe this apparently favoured isomerization. Alternative procedures were then investigated that sought to convert the pyrrolidine (1) into precursors to retronecine, and notable successes were obtained with the addition of the amine (21) to both nitroethene and ethyl 2-diethylphosphonoacrylate. However, not only were these precursors resistant to further transformations into retronecine , but also the problem of epimerization again arose. Consequently, AM1 calculations were again employed, and an X-ray structure determination of ethyl (7R,8R)-7-benzyloxy-1-benzyloxymethyl-5,6,7,8-tetrahydro-3H-pyrrolizine-2-carboxylate (39) is reported. Attempts to convert (39) into a diastereoisomer of retronecine were unsuccessful.

https://doi.org/10.1071/CH9930805

© CSIRO 1993

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