Département de chimie moléculaire

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.