Catalytic C2 prenylation of unprotected indoles: Late-stage diversification of peptides and two-step total synthesis of tryprostatin B
| Autor: | Qing-An Chen, Yancheng Hu, Heng Liu, Hao Zheng, Ying Li, Gong Zhang, Ding-Wei Ji |
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| Rok vydání: | 2021 |
| Předmět: |
Indole test
Chemistry Tryptophan Total synthesis Regioselectivity 02 engineering and technology General Medicine 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis Acid catalysis Prenylation Tryprostatin B 0210 nano-technology |
| Zdroj: | Chinese Journal of Catalysis. 42:1593-1607 |
| ISSN: | 1872-2067 |
| Popis: | C2 prenylated indoles are widespread in a variety of bioactive natural alkaloids. Therefore, the selective installation of prenyl group at C2 position of NH indoles is of great significance. However, the known protocols generally require a multi-step procedure and stoichiometric promoters. Herein we develop a one-step C2 prenylation of NH indole with cheap tert-prenyl alcohol enabled by acid catalysis. Salient features include good regioselectivity, step- and atom-economy, broad substrate scope, and simple catalytic system. The mechanistic investigations demonstrate that both C2 prenylation and C3 prenylation/migration pathways are engaged in the reaction. Notably, this practical strategy can be applied to the late-stage diversification of tryptophan-based peptides and concise synthesis of tryprostatin B. |
| Databáze: | OpenAIRE |
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