Indole alkaloids with self-activated sp2 CH bond from Alstonia scholaris. Issue 21 (21st May 2020)

• Record Type: Journal Article
• Authors: Wei, Xin; Qin, Xu-Jie; Jin, Qiong; Yu, Hao-Fei; Ding, Cai-Feng; Khan, Afsar; Liu, Ya-Ping; Xia, Chengfeng; Luo, Xiao-Dong
• Is Part Of: Tetrahedron letters. Volume 61:Issue 21(2020)
• Publication Date: 2020-05-21
• Subjects: Alstonia scholaris -- Indole alkaloids -- Nor-C17 strychnan -- CH self-activation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151894
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Two novel monoterpenoid indole alkaloids from Alstonia scholaris . nor -C17 Strychnan indole. Highly modified strychnan with an additional furan ring between C-16/19. ECD calculations. sp 2 CH self-activation and deuteration of natural products. Abstract: Alstoniascholarines T (1 ) and U (2 ), two novel monoterpenoid indole alkaloids from Alstonia scholaris, enabled an unexpected deuteration via activation of the sp 2 CH bond without any catalysts under room temperature. Structurally, alkaloid 1 represented the rare nor -C17 strychnan indole, and compound 2 possessing highly modified strychnan skeleton with an additional furan ring between C-16/19. This finding presented the detailed description of natural products with sp 2 CH self-activation and deuteration, which may shed a light on the CH functionalization blocked by the expensive metal catalysts and/or rather harsh reaction conditions.