Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France.
Org Lett. 2012 Feb 17;14(4):1042-5. doi: 10.1021/ol203396s. Epub 2012 Jan 31.
The SmI(2)-mediated cross-coupling of nitrones with β-silyl-α,β-unsaturated esters, followed by zinc reduction, allows an efficient and highly diastereoselective preparation of β-silyl lactams, which are precursors of β-hydroxy lactams through Tamao-Fleming oxidation. By applying the method to a cyclic, carbohydrate-derived nitrone, a new synthesis of (+)-australine has been realized in only 11 steps and in 21% overall yield from L-xylose.
SmI(2)介导的硝酮与β-硅基-α,β-不饱和酯的交叉偶联，接着进行锌还原，允许高效和高度非对映选择性地制备β-硅基内酰胺，这些内酰胺通过 Tamao-Fleming 氧化是β-羟基内酰胺的前体。通过将该方法应用于环状、碳水化合物衍生的硝酮，仅通过 L-木糖经过 11 步反应以 21%的总收率实现了 (+)-澳瑞他汀的新合成。
