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Enantioselective construction of cyclic quaternary centers: (-)-mesembrine.

Authors
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Volume
66
Issue
1
Pages
143–147
Identifiers
PMID: 11429891
Source
Medline
License
Unknown

Abstract

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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