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
Revue
Org. Lett.
Volume
14
Pagination
1042–1045
ISSN
1523-7052
Soumis le 12 avril 2018