1416353-00-8Relevant articles and documents
Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids
He, Weigang,Hu, Jiadong,Wang, Pengyan,Chen, Le,Ji, Kai,Yang, Siyu,Li, Yin,Xie, Zhilong,Xie, Weiqing
, p. 3806 - 3809 (2018)
A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N′-dioxide Sc(OTf)3 catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3′-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(?)-tubifoline, (?)-tubifolidine, (?)-dehydrotubifoline] was achieved in 10–11 steps.
