SmI2-Mediated Cross-Coupling of Nitrones with β-Silyl Acrylates: Synthesis of (+)-Australine.
The SmI2-mediated cross-coupling of nitrones with beta-silyl-alpha,beta-unsatd. esters, followed by zinc redn., allows an efficient and highly diastereoselective prepn. of beta-silyl lactams, which are precursors of beta-hydroxy lactams through Tamao-Fleming oxidn. By applying the method to a cyclic, carbohydrate-derived nitrone, a new synthesis of (+)-australine (I) has been realized in only 11 steps and in 21% overall yield from L-xylose.
Références
- Titre
- SmI2-Mediated Cross-Coupling of Nitrones with β-Silyl Acrylates: Synthesis of (+)-Australine.
- Type de publication
- Article de revue
- Année de publication
- 2012
- Auteurs
- Gilles, Pierre, and Py Sandrine
- Revue
- Org. Lett.
- Volume
- 14
- Pagination
- 1042–1045
- ISSN
- 1523-7052
Soumis le 12 avril 2018