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

doi:10.6023/cjoc202310009

有机化学 ›› 2024, Vol. 44 ›› Issue (4): 1160-1180.DOI: 10.6023/cjoc202310009 上一篇下一篇

综述与进展

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^,^*()

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 Peng^a, Yuxiang Zhao^b, Shaojian Pu^a, Juan Luo^b, Teng Liu^b(), Yingchun Miao^b(), Xianfu Shen^b()

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

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摘要/Abstract

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.

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

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

引用此文

彭天凤, 赵玉祥, 浦绍健, 罗娟, 刘腾, 缪应纯, 沈先福. 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[J]. 有机化学, 2024, 44(4): 1160-1180.

Tianfeng Peng, Yuxiang Zhao, Shaojian Pu, Juan Luo, Teng Liu, Yingchun Miao, Xianfu Shen. Recent Advances in Total Synthesis of Prenylated Indole Alkaloids by Transition Metal-Catalyzed Reactions as the Key Step[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1160-1180.

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图/表 21

图1. 具有代表性的异戊烯基吲哚生物碱

Figure 1. Representative prenylated indole alkaloids

图式1. Tamaru课题组的(+)-ardeemin的形式合成

Scheme 1. Tamaru’s formal total synthesis of (+)-ardeemin

图式2. Trost课题组的(–)-Spirtryprostatin B的不对称合成

Scheme 2. Trost’s asymmetric total synthesis of (–)-spirtryprostatin B

图式3. Trost课题组的(+)-Flustramide A, (+)-Flustramine A, (+)-Flustramide B和(+)-Flustramine B的不对称合成

Scheme 3. Trost’s asymmetric synthesis of (+)-flustramide A, (+)-flustramine A, (+)-flustramide B and (+)-flustramine B

图式4. Fukuyama课题组的(–)-Spirtryprostatin A的不对称全合成

Scheme 4. Fukuyama’s asymmetric total synthesis of (–)-spirtryprostatin A

图式5. 游书力课题组的钯催化不对称合成(–)-Flustramine B和(–)-Mollenine A

Scheme 5. You’s Pd catalytic asymmetric total synthesis of (–)-flustramine B and (–)-mollenine A

图式6. Carreira课题组的异戊烯吲哚生物碱(+)-Aszonalenin和(–)-Brevicompanine B的合成

Scheme 6. Carreira’s synthesis of prenylated indole alkaloids (+)-aszonalenin and (–)-brevicompanine B

图式7. Stark课题组的(–)-Amauromine, (–)-Novoamauromine和epi-Amauromine的合成

Scheme 7. Stark’s total synthesis of (–)-amauromine, (–)-novoamauromine and epi-amauromine

图式8. 杨玉荣课题组的铱催化不对称合成(–)-Communesin F

Scheme 8. Yang’s Ir-catalytic asymmetric total synthesis of (–)-communesin F

图式9. Baran课题组的(+)-Verruculogen和(+)-Fumitremorgin A的全合成

Scheme 9. Baran’s total synthesis of (+)-verruculogen and (+)-fumitremorgin A

图式10. Sarpong课题组的(+)-Malbrancheamide C, (+)-Malbrancheamide B和(+)-Stephacidin A的全合成

Scheme 10. Sarpong’s total synthesis of (+)-malbrancheamide C, (+)-malbrancheamide B and (+)-stephacidin A

图式11. Sarpong课题组的(+)-Stephacidin B、(+)-Waikialoid及其类似物的不对称合成

Scheme 11. Sarpong’s asymmetric total synthesis of (+)-stephacidin B, (+)-waikialoid and its congeners

图式12. 沈先福课题组的(–)-Spirotryprostatin A不对称合成

Scheme 12. Shen’s asymmetric total synthesis of (–)-spirotryprostatin A

图式13. 谢卫青课题组的(–)-Dihydrospirotryprostatin B不对称合成

Scheme 13. Xie’s asymmetric total synthesis of (–)-dihydrospirotryprostatin B

图式14. 秦勇课题组的(–)-Formylardeemin 和(–)-Ardeemin不对称合成

Scheme 14. Qin’s asymmetric total synthesis of (–)-formylardeemin and (–)-ardeemin

图式15. Tokuyama课题组的(+)-Novoamauromine和(–)-epi-Amauromine不对称合成

Scheme 15. Tokuyama’s asymmetric total synthesis of (+)-novoamauromine and (–)-epi-amauromine

图式16. 王海飞课题组的(–)-Spirotryprostatin A不对称合成

Scheme 16. Wang’s asymmetric total synthesis of (–)-spirotryprostatin A

图式17. Ting课题组的(+)-13-Oxoverruculogen不对称合成

Scheme 17. Ting’s asymmetric total synthesis of (+)-13-oxoverruculogen

图式18. 张洪彬课题组的(–)-Spirtryprostatins A, B和(–)-6-Methoxy-spirotryprostatin B的不对称合成

Scheme 18. Zhang’s asymmetric total synthesis of (–)-spirtryprostatins A, B and (–)-6-methoxy-spirotryprostatin B

图式19. 李超忠课题组的(+)-Noatamide I, (+)-Noatamide R, (+)-Noatamide F和(–)-Sclerotamide的不对称合成

Scheme 19. Li’s asymmetric total synthesis of (+)-noatamide I, (+)-noatamide R, (+)-noatamide F and (–)-sclerotamide

图式20. 谢卫青课题组的(–)-Debromoflustramine的不对称合成

Scheme 20. Xie’s asymmetric total synthesis of (–)-debromoflustramine A

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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

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

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