A Highly Stereoselective Asymmetric Synthesis of (−)-Lobeline and (−)-Sedamine

A Highly Stereoselective Asymmetric Synthesis of (−)-Lobeline and (−)-Sedamine

A highly stereoselective asymmetric synthesis of (−)-sedamine and (−)-lobeline is described from benzaldehyde in 16 and 17 steps with an overall yield of 20% and 14%, respectively. The key intermediate syn-3,4-epoxyalcohol was prepared in a highly diastereomeric fashion (>99% ee, dr) and served a...

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Veröffentlicht in:Journal of organic chemistry 2002-12, Vol.67 (26), p.9192-9199
Hauptverfasser: Felpin, François-Xavier, Lebreton, Jacques
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - analysis
Alkaloids - chemical synthesis
Alkaloids - chemistry
Catalysis
Chemistry
Chemistry, Organic - methods
Chromatography, High Pressure Liquid
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Lobelia - chemistry
Lobeline - analysis
Lobeline - chemical synthesis
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Organic chemistry
Piperidines - analysis
Piperidines - chemical synthesis
Plants, Medicinal - chemistry
Preparations and properties
Stereoisomerism
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Zusammenfassung:A highly stereoselective asymmetric synthesis of (−)-sedamine and (−)-lobeline is described from benzaldehyde in 16 and 17 steps with an overall yield of 20% and 14%, respectively. The key intermediate syn-3,4-epoxyalcohol was prepared in a highly diastereomeric fashion (>99% ee, dr) and served as a common intermediate for both alkaloids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020501y