Synthesis of indole alkaloid (−)-corynantheidol and formal synthesis of (−)-corynantheidine via one-pot asymmetric azaelectrocyclization
作者:Yanwu Li、Toyoharu Kobayashi、Shigeo Katsumura
DOI:10.1016/j.tetlet.2009.05.045
日期:2009.8
The highly efficient asymmetric total synthesis of indolealkaloid, (−)-corynantheidol, containing a 2,4,5-trisubstituted piperidine core, was achieved using a new version of the one-pot azaelectrocyclization reaction. The formal synthesis of (−)-corynantheidine was also achieved using the common synthetic intermediate for these corynantheines.
presence of a Pd(0) catalyst stereoselectively produced the tetracyclic aminoacetal compounds, resulting from the four-bond formation accompanying by controlling the stereochemistry at the two asymmetric centers. The produced cyclic aminoacetals can be regarded as synthetic precursors of substituted chiral piperidines, and the syntheses of 2,4- and 2,4,6-substituted piperidines were realized from the obtained