4802-79-3Relevant articles and documents
The Synthesis of (±)-1,2,3,4,6,7,12,12b-Octahydroindolo[2,3-a]quinolizine from Tryptophan and Dihydropyran
Badenock, Jeanese C.,Gribble, Gordon W.
, p. 449 - 453 (2018)
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A convenient synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
Yamanaka,Nakayama,Yanagishima,et al.
, p. 2527 - 2530 (1980)
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A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction
Park, Eunjoon,Cheon, Cheol-Hong
, p. 10265 - 10275 (2017)
A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.
Oxidative Pictet-Spengler cyclisations through acceptorless iridium-catalysed dehydrogenation of tertiary amines
Cooksey, John P.,Saidi, Ourida,Williams, Jonathan M.J.,Blacker, A. John,Marsden, Stephen P.
, (2020/12/14)
The valuable tetrahydro-β- and γ-carboline skeleta can be accessed through Pictet-Spengler cyclisation initiated by acceptorless dehydrogenation of saturated cyclic amines. The substrate scope for the β-isomers is found to be somewhat limited, but access
One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds
Song, Qiao,Liu, Yan,Cai, Linlin,Cao, Xinyu,Qian, Shan,Wang, Zhouyu
, p. 1713 - 1716 (2021/03/08)
Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the total synthesis of alkaloids such as (±)-crispine A, (±)-xylopinine, (±)-desbromoarborescidine A, (±)-harmicine and other bioactive substances.