化学
全合成
纳米技术
组合化学
立体化学
材料科学
作者
Xiaofeng Guo,Hui Shao,Zhi‐Hua Ma,Jian Sun,Zhou Qin,Yu‐Ming Zhao
出处
期刊:Organic Letters
[American Chemical Society]
日期:2024-04-02
卷期号:26 (15): 3135-3139
标识
DOI:10.1021/acs.orglett.4c00727
摘要
Herein, we present the first racemic total synthesis of the structurally complex monoterpene indole alkaloids rhynchines A–E, starting from commercially available methyl nicotinate and 3-(2-bromoethyl)-1H-indole. The success of our synthesis is attributed to the utilization of a bioinspired synthetic strategy, which facilitated the rapid construction of the pentacyclic core skeleton of the target molecules through biomimetic skeletal rearrangement and late-stage C–H oxidative cyclization. Additionally, silica-gel-promoted tautomerization played a crucial role as a strategic element in the chemical synthesis of rhynchines A and B.
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