125160-74-9Relevant academic research and scientific papers
SYNTHETIC STUDIES ON INDOLE ALKALOIDS. A STEREOCONTROLLED ENTRY TO THE CUANZINE STRUCTURAL UNIT (1)
Palmisano, Giovanni,Danieli, Bruno,Lesma, Giordano,Passarella, Daniele
, p. 3583 - 3596 (1989)
An efficient synthesis of the cuanzine precursor 4d has been achieved beginning with 8-methoxy-dihydro-β-carboline 3b and utilizing as the key step the stereocontrolled alkylation of 16a (and/or 20a) followed by Hg(II)-induced heterocyclization.The struct
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
supporting information, p. 3806 - 3809 (2018/03/05)
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.
Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines
Zheng, Nan,Chang, Yuan-Yuan,Zhang, Li-Jie,Gong, Jian-Xian,Yang, Zhen
supporting information, p. 371 - 375 (2016/05/19)
A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3·Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.
