| Autor: |
Shipe, W. D., Sorensen, E. J. |
| Zdroj: |
Organic Letters; June 2002, Vol. 4 Issue: 12 p2063-2066, 4p |
| Abstrakt: |
This Letter describes a concise, diastereoselective synthesis of the tricyclic carbon framework of the guanacastepene family of natural products. An intermolecular Diels−Alder reaction established a remote stereochemical relationship and facilitated a synthesis of allylic acetate 3, which was subsequently joined with vinylstananne 9 via a Stille coupling. An intramolecular [2 + 2] photocycloaddition then afforded complex cyclobutyl ketone 19, which underwent a stereoelectronically controlled fragmentation to the guanacastepene architecture on treatment with samarium diiodide. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
|
