Collective Asymmetric Synthesis of (−)-Antofine, (−)-Cryptopleurine, (−)-Tylophorine, and (−)-Tylocrebrine with <i>tert-</i>Butanesulfinamide as a Chiral Auxiliary
作者:Yanlong Zheng、Yuxiu Liu、Qingmin Wang
DOI:10.1021/jo500013e
日期:2014.4.18
A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (−)-antofine, (−)-cryptopleurine, (−)-tylophorine, and (−)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine
菲咯啉吲哚和菲咯啉喹嗪生物碱(-)-antofine,(-)-cryptopleurine,(-)-酪氨酸和(-)-酪蛋白的集体不对称合成是通过涉及通过有效生成手性均烯丙基胺中间体的反应序列实现的对应的叔丁烷亚磺酰基亚胺的不对称烯丙基化。从这些中间体,吡咯烷和哌啶环通过分子内S的装置构造Ñ分别2取代反应和闭环复分解反应,。是由一个的InCl的装置产生tylocrebrine - ( - )的不寻常的C5-甲氧基取代的菲部分3的催化的的反应环异构ø -炔丙基二芳基化合物。