Enantioselective Construction of Cyclic Quaternary Centers:  (−)-Mesembrine

Enantioselective Construction of Cyclic Quaternary Centers:  (−)-Mesembrine

The preparation of the crystalline amide 2 is reported. Conjugate addition to 2 proceeded with the expected high diastereocontrol to give 3. This set the stage for subsequent intramolecular alkylidene C−H insertion to give, after ozonolysis and aldol condensation, (−)-mesembrine 1. Amide 2 should be...

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Veröffentlicht in:Journal of organic chemistry 2001-01, Vol.66 (1), p.143-147
Hauptverfasser: Taber, Douglass F, Neubert, Timothy D
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Crystallography, X-Ray
Hydrolysis
Indicators and Reagents
Indole Alkaloids
Molecular Conformation
Ozone
Plants, Medicinal - chemistry
Stereoisomerism
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Zusammenfassung:The preparation of the crystalline amide 2 is reported. Conjugate addition to 2 proceeded with the expected high diastereocontrol to give 3. This set the stage for subsequent intramolecular alkylidene C−H insertion to give, after ozonolysis and aldol condensation, (−)-mesembrine 1. Amide 2 should be a useful chiron for the enantioselective construction of cyclic quaternary centers.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo001237g