Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1160-1180.DOI: 10.6023/cjoc202310009 Previous Articles     Next Articles

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过渡金属催化的关键反应在异戊烯基吲哚生物碱全合成中的研究进展

彭天凤a, 赵玉祥b, 浦绍健a, 罗娟b, 刘腾b,*(), 缪应纯b,*(), 沈先福b,*()   

  1. a 曲靖师范学院生物资源与食品工程学院 云南曲靖 655011
    b 曲靖师范学院化学与环境科学学院 云南曲靖 655011
  • 收稿日期:2023-10-08 修回日期:2023-11-10 发布日期:2023-11-23
  • 基金资助:
    国家自然科学基金(22361040); 云南省自然科学基金(202001AT070004); 云南省自然科学基金(202205AC160004); 云南省自然科学基金(202301BA070001-102); 大学生创新创业训练计划; 云南省高校绿色催化与能源材料科技创新团队; 曲靖师范学院创新团队资助项目

Recent Advances in Total Synthesis of Prenylated Indole Alkaloids by Transition Metal-Catalyzed Reactions as the Key Step

Tianfeng Penga, Yuxiang Zhaob, Shaojian Pua, Juan Luob, Teng Liub(), Yingchun Miaob(), Xianfu Shenb()   

  1. a College of Biological Resource and Food Engineering, Qujing Normal University, Qujing, Yunnan 655011
    b College of Chemistry and Environmental Science, Qujing Normal University, Qujing, Yunnan 655011
  • Received:2023-10-08 Revised:2023-11-10 Published:2023-11-23
  • Contact: E-mail: xianfu_shen@163.com;398836242@qq.com;15288404381@163.com
  • Supported by:
    National Natural Science Foundation of China(22361040); Natural Science Foundation of Yunnan Province(202001AT070004); Natural Science Foundation of Yunnan Province(202205AC160004); Natural Science Foundation of Yunnan Province(202301BA070001-102); National Innovation and Entrepreneurship Training Program for College Students; Scientific and Technological Innovation Team for Green Catalysis and Energy Material at Yunnan Institutions of Higher Learning; Program for Innovative Research Team in Qujing University

The prenylated indole alkaloids are an intriguning and important class of natural products encompassing an indole ring, or derivatives thereof (that is, spirooxindole or pseudoindowoxyl), decorated by one or more prenyl groups or the vestige of a prenyl group. They comprise a large and structurally diverse family of natural products that display a diverse range of important biological properties. Nature employs dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) as starting materials for the biosynthesis of numerous prenylated indole alkaloids. The indole core in these compounds is typically derived from L-tryptophan, or less commonly from indole-3-glycerol phosphate. Prenylation is a ubiquitous process common to almost all living organisms, and a key transformation in organic synthesis. In recent years, prenylated indole alkaloids have constantly received intensive research from synthetic chemical community and pharmacologists due to their intriguing structural motifs and diverse biological profiles. To date, the development of straightforward and efficient protocols to enable the synthesis of structurally diverse prenylated indole alkaloids is highly desirable and challenging. The recent advances in the total synthesis of prenylated indole alkaloids by transition metal-catalyzed reactions as the key step are summarized.

Key words: transition metal-catalyzed, prenylated indole alkaloids, natural products, quaternary carbon stereocenter, total synthesis