65601-15-2Relevant academic research and scientific papers
Stereocontrolled Synthesis of Exocyclic Trisubstituted Double Bonds by Stereospecific Iminium Ion-Vinylsilane Cyclizations. A Short Synthetic Route to Indoloquinolizidine Alkaloids
Overman, Larry E.,Malone, Thomas C.
, p. 5297 - 5300 (2007/10/02)
The reaction of (Z)- and (E)-trisubstituted vinylsilanes 9 and 10 with paraformaldehyde and acid proceeded with >98percent retention of configuration to give indoloquinolizidines 13 and 3 in excellent yield.This is the first demonstration that iminium ion-vinylsilane cyclizations occur with complete retention of configuration with either vinylsilane stereoisomer.The simple indole alkaloid dl-deplancheine (3) was prepared in a stereocontrolled fashion in 26percent overall yield from commercially available 1-(trimethylsilyl)propyne.
