A convergent total synthesis of a new antiepileptic ceramide and its triacetyl derivative using olefin cross metathesis
作者:Partha Ghosal、Vikas Kumar、Arun K. Shaw
DOI:10.1016/j.tet.2010.07.049
日期:2010.9
A convergent total synthesis of a new antiepileptic ceramide 1b and its triacetyl derivative 1b′ was completed by using two important C–C bond forming reactions, Wittig methylenation and olefin cross metathesis as the key steps. The easily available 3,4,6-tri-O-benzyl-d-galactal was used as a chiral pool for the synthesis of highly functionalized amide 3 and the commercially available 1,12-dodecanediol
新的抗癫痫性神经酰胺1b及其三乙酰基衍生物1b '的聚合总合成通过两个重要的C–C键形成反应(维蒂希甲基化和烯烃交叉复分解)作为关键步骤完成。在容易获得的3,4,6-三- ö苄基d -galactal用作高度官能化的酰胺合成手性池3和市售1,12-十二烷二醇的长链烯烃对应物4。通过使用酰胺3和长链末端烯烃4之间的烯烃交叉复分解,安装了新的神经酰胺1b的长烃链。 然后加氢。