Copper(I)‐Catalyzed Cascade Cyclization to the Total Synthesis of Hexahydropyrroloindole Alkaloids: Flustramine B and Debromoflustramine B. Issue 21 (1st June 2021)

• Record Type: Journal Article
• Authors: Shen, Xianfu; Peng, Tianfeng; Wang, Fan; Li, Shumin; Lei, Xingfu; Yunxiao, ; Wang, ; Cheng, Feixiang; Liu, Teng
• Is Part Of: ChemistrySelect. Volume 6:Issue 21(2021)
• Page Start: 5195
• Page End: 5197
• Publication Date: 2021-06-01
• Subjects: Alkaloids -- Cascade Cyclization -- Copper -- Hexahydropyrroloindole -- Tetrasubstituted stereocenters; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202101134
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: In this report, we have accomplished the total synthesis of two bioactive hexahydropyrroloindole (HPI) alkaloids bearing a C3a tetrasubstituted stereocenters substituted by isopentenyl. This route was based on Cu‐catalyzed cascade arylation‐alkylation sequence in one‐pot as a key step, providing Flustramine B and Debromoflustramine B with 9 steps in 37.6 % and 31.1 % overall yields, respectively. Abstract : Copper(I)‐Catalyzed Cascade Cyclization to the Total Synthesis of Hexahydropyrroloindole Alkaloids: Flustramine B and Debromoflustramine B In this work, we have accomplished the total synthesis of two bioactive hexahydropyrroloindole (HPI) alkaloids bearing a C3a tetrasubstituted stereocenters substituted by isopentenyl. Our route was based on Cu‐catalyzed cascade arylation‐alkylation sequence in one‐pot as a key step, providing Flustramine B and Debromoflustramine B with 9 steps in 37.6 % and 31.1 % overall yields, respectively.