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  

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

作　　者：彭天凤 赵玉祥 浦绍健 罗娟 刘腾 缪应纯 沈先福 Peng Tianfeng;Zhao Yuxiang;Pu Shaojian;Luo Juan;Liu Teng;Miao Yingchun;Shen Xianfu(College of Biological Resource and Food Engineering,Qujing Normal University,Qujing,Yunnan 655011;College of Chemistry and Environmental Science,Qujing Normal University,Qujing,Yunnan 655011)

机构地区：[1]曲靖师范学院生物资源与食品工程学院,云南曲靖655011 [2]曲靖师范学院化学与环境科学学院,云南曲靖655011

出　　处：《有机化学》2024年第4期1160-1180,共21页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.22361040);云南省自然科学基金(Nos.202001AT070004,202205AC160004,202301BA070001-102);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和曲靖师范学院创新团队资助项目。

摘　　要：异戊烯基吲哚生物碱是一类结构有趣和重要的天然产物家族化合物,其典型结构特征是有一个吲哚环或其衍生物(即螺环氧化吲哚或假吲哚),由一个或多个异戊烯基或异戊烯基的残基修饰.异戊烯基吲哚生物碱组成了一个庞大和结构多样化的具有广泛且重要的生物活性天然产物家族化合物.自然界以焦磷酸二甲基烯丙基(DMAPP)和焦磷酸异戊烯基(IPP)为起始原料,生物合成了许多异戊烯基吲哚生物碱,而异戊烯基吲哚生物碱的吲哚核心通常来源于L-色氨酸,或者少部分来源于吲哚-3-甘油磷酸酯.异戊烯基化是几乎所有生物普遍存在的过程,是有机合成中的关键转化.近年来,异戊烯基吲哚生物碱因其独特的结构单元和多样的生物学活性,受到合成化学家和药理学家的持续深入研究.迄今为止,发展一类直接和高效的方法来合成结构多样的异戊烯基吲哚生物碱是非常理想的,同时也是非常具有挑战性的研究工作.综述了近期过渡金属催化的关键反应在异戊基化吲哚生物碱全合成中的研究进展.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.

关 键 词：过渡金属催化 异戊烯基吲哚生物碱 天然产物 手性季碳中心 全合成 

分 类 号：O621.251[理学—有机化学] O629.3[理学—化学]