Total Synthesis of (+)-Epiquinamide

The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provi...

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Bibliographic Details
Published in:Organic letters 2005-09, Vol.7 (18), p.4005-4007
Main Authors: Wijdeven, Marloes A, Botman, Peter N. M, Wijtmans, Roel, Schoemaker, Hans E, Rutjes, Floris P. J. T, Blaauw, Richard H
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Cyclization
Molecular Conformation
Molecular Structure
Quinolizines - chemical synthesis
Quinolizines - chemistry
Stereoisomerism
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Summary:The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provide the bicyclic skeleton.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0515715