Tetrahedron 2018-03-10

Diastereoselective approach to trans-5-hydroxy-6-substitutedethanone-2-piperidinones: Scalable syntheses of (+)-febrifugine and (+)-halofuginone

Chen Wang, Yi-Wen Liu, Zhu Zhou, Chang-Mei Si, Xun Sun, Bang-Guo Wei

文献索引：10.1016/j.tet.2018.03.022

摘要

An efficient diastereoselective approach to access trans-5-hydroxy-6-substitutedethanone-2-piperidinones skeleton has been developed through sequential addition-deprotection-cyclization process involving aldimine 6 with substituted acetones. The diastereoselectivity of substitution at C-6 position of 2-piperidinone was controlled by α-siloxyl group and chiral sulfinamide moiety. In addition, the utility of this effective approach is demonstrated by the scalable syntheses of (+)-febrifugine (2) and (+)-halofuginone (4).