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.