486-71-5Relevant articles and documents
A Concise Asymmetric Total Synthesis of (+)-Epilupinine
Tsutsumi, Tomohiro,Karanjit, Sangita,Nakayama, Atsushi,Namba, Kosuke
, p. 2620 - 2624 (2019/04/30)
Asymmetric total synthesis of (+)-epilupinine was achieved in just three steps using only commercially available common reagents. The total synthesis involved alkylations of N-nosylamide, ozone oxidation, and sequential reactions of the removal of the nosyl group, intramolecular dehydrative condensation, intramolecular Mannich reaction catalyzed by l-proline, and a reduction.
Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base
Park, Yongho,Schindler, Corinna S.,Jacobsen, Eric N.
supporting information, p. 14848 - 14851 (2016/11/29)
An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure-enantioselectivity relationship studies and mechanistic analysis point to a dual role of the catalyst wherein the thiourea moiety of the catalyst is engaged in both anion binding and Lewis base activation of a substrate.
Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition
Su, Deyong,Wang, Xinyan,Shao, Changwei,Xu, Jimin,Zhu, Rui,Hu, Yuefei
supporting information; experimental part, p. 188 - 194 (2011/03/21)
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 (R)-N-(3-nitropropyl)-2-vinylpiperidine or (R)-(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-(N,N-dialkylamino)propanols into 3-(N,N-dialkylamino)propanal oximes without using the corresponding aldehydes.