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Asymmetric Total Synthesis of Apocynaceae Hydrocarbazole Alkaloids (+)-Deethylibophyllidine and (+)-Limaspermidine.
- Source :
-
Journal of the American Chemical Society . 4/1/2015, Vol. 137 Issue 12, p4267-4273. 7p. - Publication Year :
- 2015
-
Abstract
- An unprecedented asymmetric catalytic tandem aminolysis/aza-Michael addition reaction of spirocyclic para-dienoneimides has been designed and developed through organocatalytic enantioselective desymmetrization. A unified strategy based on this key tandem methodology has been divergently explored for the asymmetric total synthesis of two natural Apocynaceae alkaloids, (+)-deethylibophyllidine and (+)-limaspermidine. The present studies not only enrich the tandem reaction design concerning the asymmetric catalytic assembly of a chiral all-carbon quaternary stereocenter contained in the densely functionalized hydrocarbazole synthons but also manifest the potential for the application of the asymmetric catalysis based on the para-dienone chemistry in asymmetric synthesis of natural products. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00027863
- Volume :
- 137
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 102925236
- Full Text :
- https://doi.org/10.1021/jacs.5b01926