Enantioselective construction of cyclic quaternary centers: (-)-mesembrine.
- Published Article
The Journal of organic chemistry
- Publication Date
Jan 12, 2001
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.
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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/11429891