10.1021/jo101910r.s001
Deyong Su
Deyong
Su
Xinyan Wang
Xinyan
Wang
Changwei Shao
Changwei
Shao
Jimin Xu
Jimin
Xu
Rui Zhu
Rui
Zhu
Yuefei Hu
Yuefei
Hu
Total Synthesis of (+)-Epilupinine via An Intramolecular Nitrile Oxide-Alkene Cycloaddition
American Chemical Society
2011
quinolizidine skeleton
INOC
CycloadditionTotal
conversion
Fukuyama
intermediate
aldehyde
Epilupinine
Nitrile
method
synthesis
oxime
construction
epilupinine
task
Total Synthesis
Intramolecular
2011-01-07 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_Epilupinine_via_An_Intramolecular_Nitrile_Oxide_Alkene_Cycloaddition/2699959
Total synthesis of (+)-epilupinine was accomplished in nine steps and in 48% overall yield, in which INOC was used as the key step for the construction of the quinolizidine skeleton. We found that it was an extremely difficult task to prepare the key intermediates (<i>R</i>)-<i>N</i>-(3-nitropropyl)-2-vinylpiperidine or (<i>R</i>)-(2-vinylpiperid-1-yl)propanal by routine methods. Thus, by using Fukuyama’s oxime synthesis, a general method was developed for highly efficient conversion of 3-(<i>N</i>,<i>N</i>-dialkylamino)propanols into 3-(<i>N</i>,<i>N</i>-dialkylamino)propanal oximes without using the corresponding aldehydes.