Highly Enantioenriched Tetrahydropyridines from Chiral Organosilanes: Application to the Synthesis of Quinolizidine Alkaloid ()-217A
摘要：
The tetrahydropyridine and piperidine subunits are widely found in biologically active molecules and natural products. Alhough considerable synthetic efforts have been made to reach these systems, there are few direct methods available for the preparation of enantionenriched tetrahydropyridines. A Lewis acid-promoted intramolecular imine crotylation is described and results in direct access to enantioenriched 2,6-cis- and 2,6-trans-3-trans-trisubstituted tetrahydropyridines with high diastereoselectivity. An example of the application of this methodology was demonstrated in an expedient total synthesis of (-)-quinolizidine 217A. The absolute stereochemistry of this natural product was established by the total synthesis.
展开
关键词：
pyridine derivatives diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism alkaloids
DOI：
10.1021/ja028937i
被引量：
年份：
2003
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用！
