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Straightforward Construction of Fused 6,7,5-Tricarbocyclic Systems by Tandem [5 + 2]/[4 + 2] Cycloadditions.
- Source :
-
The Journal of organic chemistry [J Org Chem] 1999 Feb 05; Vol. 64 (3), pp. 966-970. - Publication Year :
- 1999
-
Abstract
- One-pot coupling of an intramolecular thermal [5C + 2C] pyrone-alkene cycloaddition to a [4C + 2C] Diels-Alder reaction provides immediate access to 6,7,5-tricarbocyclic systems bearing a 1,4-oxa-bridge in the seven-membered carbocycle. The transformation entails the net formation of four carbon-carbon bonds and creates three new cycles and a minimum of five new stereocenters. Preliminary attempts to open the oxa-bridge by reaction of the adducts with samarium diiodide and trimethylsilyl triflate led to relatively unexpected deoxygenated and aromatized products.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 64
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 11674170
- Full Text :
- https://doi.org/10.1021/jo982050g