197365-59-6Relevant articles and documents
Asymmetric intramolecular Friedel–Crafts reaction catalyzed by a spiropyrrolidine organocatalyst: Enantioselective construction of indolizine and azepine frameworks
Zhang, Yi-Hang,Yuan, Yong-Hai,Zhang, Shu-Yu,Tu, Yong-Qiang,Tian, Jin-Miao
, p. 4015 - 4018 (2018)
The asymmetric intramolecular Friedel–Crafts type Michael reaction of α,β-unsaturated aldehyde with pyrrole, catalyzed by a spiropyrrolidine (SP)-type organocatalyst, has been accomplished, which allows the construction of a series of azepine and indolizi
Br?nsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: Total syntheses of (±)-tashiromine and (±)-indolizidine 209I
Olivier, Wesley J.,Gardiner, Michael G.,Bissember, Alex C.,Smith, Jason A.
, p. 5436 - 5441 (2018/05/16)
This study provides the first report of the construction of tetrahydroindolizines and tetrahydropyrrolo[1,2-a]azepines via Br?nsted acid-mediated annulation of pyrroles featuring N-tethered α,β-unsaturated esters. In addition, the Br?nsted acid-catalyzed cyclization of pyrroles featuring pendant α,β-unsaturated ketones was applied to complete total syntheses of the indolizidine alkaloids (±)-tashiromine and (±)-indolizidine 209I.
A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime π-cation cyclization
Gage, Jennifer L.,Branchaud, Bruce P.
, p. 7007 - 7010 (2007/10/03)
Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.
