(-)-Deoxoprosophylline的不对称合成(英文)

Asymmetric total synthesis of (-)-deoxoprosophylline

报道了一条哌啶生物碱(-)-Deoxoprosophylline的不对称合成方法.采用二碘化钐促进的手性叔丁基甲磺亚胺10与取代醛11交叉偶联为关键技术,构筑重要中间体——反式羟甲基化β-氨基醇9的立体化学,该反应的收率为77%,立体选择性为99%.这种高选择性地合成反式羟甲基化β-氨基醇的方法可方便地应用于多种含有2-羟甲基-6-取代-3-羟基哌啶生物碱的不对称合成中.

The SmI2 induced cross-coupling of chiral N-tert-butanesulfinyl imine 10 with aldehyde 11 to form hydroxymethyl-β-amino alcohol 9 （yield, 77%） with high diastereoselectivity （〉99%, de） is described in this paper. It has been used as the key step for asymmetric synthesis of （--）-deoxoprosophylline 1. Moreover, our route features the formation of anti-hydroxymethyl-β-amino alcohol, which might be generally applicable in the synthesis of various 2-hydroxymethyl-6-alkylated-3- hydroxy piperidine alkaloids and their deoxygenated derivatives with structural and biological importance.