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Utilization of 1-Aryl-2,2-dibromocyclopropanes in Synthetic Approaches to Phenanthroquinolizidine and Phenanthroindolizidine Alkaloids

Banwell, Martin; Sydnes, Magne

Description

The 1-aryl-2,2-dibromocyclopropane 8 was treated with silver acetate in acetic acid to give the allylic acetate 19. Exposure of the derived chloride 26 to racemic 2-piperidinemethanol (7) then afforded the allylic amine 6, which engaged in a Pd(0)-catalyzed cross-coupling reaction with arylboronate 29 to provide the cis-stilbene 25. The chloride 4 (X = Cl) derived from compound 25 failed to cyclize in the presence of base to give the desired phenanthroquinolizidine alkaloid julandine 1. This...[Show more]

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
URI: http://hdl.handle.net/1885/78378
Source: Australian Journal of Chemistry
DOI: 10.1071/CH03292

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