A catalytic -deacylative alkylation approach to hexahydropyrrolo[2,3-]indole alkaloids

• Published in: Chemical communications (Cambridge, England) England), 2018-08, Vol.54 (65), p.983-986
• Main Authors: Kumar, Nivesh, Maity, Arindam, Gavit, Vipin R, Bisai, Alakesh
• Format: Article
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c8cc04117b

A versatile unprecedented strategy to diversely functionalized hexahydropyrrolo[2,3- b ]indole alkaloids is described in high chemical yields. The synthesis features a key Pd(0)-catalyzed deacylative alkylation of N -acyl 3-substituted indoles using only 1 mol% of Pd(PPh 3 ) 4 . The scope of this methodology is further defined in the asymmetric synthesis of pyrroloindolines using a diastereoselective approach. An efficient synthetic strategy to diversely functionalized hexahydropyrrolo[2,3- b ]indole alkaloids is described featuring a key Pd(0)-catalyzed deacylative alkylation of N -acyl 3-substituted indoles. The reaction can be performed only using 1 mol% of Pd(PPh 3 ) 4 in the presence of 1.2 equivalent of both triethylborane and KO t Bu.