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Synthesis of enantiomerically pure hydrinden-2-ones and benz[e]inden-2-ones via asymmetric alkylations of chiral bicyclic lactams
- Source :
- The Journal of Organic Chemistry. 58:7507-7515
- Publication Year :
- 1993
- Publisher :
- American Chemical Society (ACS), 1993.
-
Abstract
- A route to the titled compounds in >99% ee was achieved from sequential diastereoselective alkylations of chiral, nonracemic bicyclic lactams 6 and 15. An intramolecular addition of the organolithium species derived from 17a-c and 28a-d gave, after hydrolysis, diketones 25a-c and 30a-d, which were cyclized to the titled compounds 4a-c and 31a-d. As an example of the versatility of this method, the ABC ring system of the triterpene stelliferin A, isolated from marine organisms, was prepared in high enantiomeric excess
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 58
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi...........3ca29c9d25a1cf968f6667f103839022