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

doi:10.6023/cjoc202310009

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

REVIEWS

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

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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 21

Figure 1. Representative prenylated indole alkaloids

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

References 44

[1]	Lindel T.; Marsch N.; Adla S. K. Top. Curr. Chem. 2011, 309, 67.
[2]	Li S.-M. Nat. Prod. Rep. 2010, 27, 57. doi: 10.1039/B909987P
[3]	Williams R. M.; Stocking E. M.; Sanz-Cervera J. F. Top. Curr. Chem. 2000, 209, 97.
[4]	Tanner M. E. Nat. Prod. Rep. 2015, 32, 88. doi: 10.1039/C4NP00099D
[5]	Miller K. A.; Williams R. B. Chem. Soc. Rev. 2009, 38, 3160. doi: 10.1039/b816705m
[6]	Walsh C. T.; Garneau-Tsodikova S.; Gatto G. J. Jr. Angew. Chem., Int. Ed. 2005, 44, 7342. doi: 10.1002/anie.v44:45
[7]	Palsuledesai C. C.; Distefano M. D. ACS Chem. Biol. 2015, 10, 51. doi: 10.1021/cb500791f pmid: 25402849
[8]	Jeong A.; Auger S. A.; Maity S.; Fredriksen K.; Zhong R.; Li L.; Distefano M. D. ACS Chem. Biol. 2022, 17, 2863. doi: 10.1021/acschembio.2c00486
[9]	Klas K. R.; Kato H.; Frisvad J. C.; Yu F. G.; Newmister S. A.; Fraley A. E.; Sherman D. H.; Tsukamoto S.; Williams R. M. Nat. Prod. Rep. 2018, 35, 532. doi: 10.1039/C7NP00042A
[10]	Ishikura M.; Abe T.; Choshi T.; Hibino S. Nat. Prod. Rep. 2013, 30, 694. doi: 10.1039/c3np20118j pmid: 23467716
[11]	Ishikura M.; Abe T.; Choshi T.; Hibino S. Nat. Prod. Rep. 2015, 32, 1389. doi: 10.1039/c5np00032g pmid: 26151910
[12]	Oldfield E.; Lin F.-Y. Angew. Chem., Int. Ed. 2012, 51, 1124. doi: 10.1002/anie.201103110 pmid: 22105807
[13]	Sacchettini J. C.; Poulter C. D. Science 1997, 277, 1788. doi: 10.1126/science.277.5333.1788 pmid: 9324768
[14]	Walsh C. T.; Garneau-Tsodikova S.; Gatto G. J. Jr. Angew. Chem., Int. Ed. 2005, 44, 7342. doi: 10.1002/anie.v44:45
[15]	Chang W.-C.; Song H.; Liu H.-W.; Liu P. Curr. Opin. Chem. Biol. 2013, 17, 571. doi: 10.1016/j.cbpa.2013.06.020
[16]	Hu Y.-C.; Ji D.-W.; Zhao C.-Y.; Zheng H.; Chen Q.-A. Angew. Chem., Int. Ed. 2019, 58, 5438. doi: 10.1002/anie.v58.16
[17]	Zhao C.-Y.; Liu Y.-Y.; Zhang X.-X.; He G.-C.; Liu H.; Ji D.-W.; Hu Y.-C.; Chen Q.-A. Angew. Chem., Int. Ed. 2022, 61, e202207202. doi: 10.1002/anie.v61.32
[18]	Chang X. X.; Zhang F. Q.; Zhu S. B.; Yang Z.; Feng X. M.; Liu Y. B. Nat. Commun. 2023, 14, 3876. doi: 10.1038/s41467-023-39633-9
[19]	Zhang G.; Zhao C.-Y.; Min X.-T.; Li Y.; Zhang X.-X.; Liu H.; Ji D.-W.; Hu Y.-C.; Chen Q.-A. Nat. Catal. 2022, 5, 708. doi: 10.1038/s41929-022-00825-z
[20]	Itoh J.; Han S. B.; Krische M. J. Angew. Chem., Int. Ed. 2009, 48, 6313. doi: 10.1002/anie.v48:34
[21]	Kimura M.; Futamata M.; Mukai R.; Tamaru Y. J. Am. Chem. Soc. 2005, 127, 4592. doi: 10.1021/ja0501161
[22]	Usui I.; Schmidt S.; Keller M.; Breit B. Org. Lett. 2008, 10, 1207. doi: 10.1021/ol800073v
[23]	Sundararaju B.; Achard M.; Demerseman B.; Toupet L.; Sharma G. V. M.; Bruneau C. Angew. Chem., Int. Ed. 2010, 49, 2782. doi: 10.1002/anie.200907034 pmid: 20229550
[24]	Yang H. W.; Fang L.; Zhang M.; Zhu C. J. Eur. J. Org. Chem. 2009, 5, 666.
[25]	Hu Y.-C.; Ji D.-W.; Zhao C.-Y.; Zheng H.; Chen Q.-A. Angew. Chem., Int. Ed. 2019, 58, 5438. doi: 10.1002/anie.v58.16
[26]	Trost B. M.; Stilels D. T. Org. Lett. 2008, 10, 3701. doi: 10.1021/ol8013073
[27]	Trost B. M.; Malhotra S.; Chan W. H. J. Am. Chem. Soc. 2011, 133, 7328. doi: 10.1021/ja2020873
[28]	Kitahara K.; Shimokawa J.; Fukuyama T. Chem. Sci. 2014, 5, 904. doi: 10.1039/C3SC52525B
[29]	Tu H.-F.; Zhang X.; Zheng C.; Zhu M.; You S.-L. Nat. Catal. 2018, 1, 601. doi: 10.1038/s41929-018-0111-8
[30]	Ruchti J.; Carreira E. M. J. Am. Chem. Soc. 2014, 136, 16756. doi: 10.1021/ja509893s
[31]	Müller J. M.; Stark C. B. W.; Angew. Chem., Int. Ed. 2016, 55, 4798. doi: 10.1002/anie.201509468 pmid: 26969898
[32]	Liang X.; Zhang T.-Y; Zeng X.-Y.; Zheng Y.; Wei K.; Yang Y.-R. J. Am. Chem. Soc. 2017, 139, 3364. doi: 10.1021/jacs.7b00854 pmid: 28219006
[33]	Feng Y.; Holte D.; Zoller J.; Umemiya S.; Simke L. R.; Baran P. S. J. Am. Chem. Soc. 2015, 137, 10160. doi: 10.1021/jacs.5b07154 pmid: 26256033
[34]	Mukai K.; de Sant’Ana D. P.; Hirooka Y.; Mercado-Marrin E. V.; Stephens D. E.; Kou K. G. M.; Richter S. C.; Kelley N.; Sarpong R. Nat. Chem. 2018, 10, 38. doi: 10.1038/nchem.2862 pmid: 29256515
[35]	Frebault F. C.; Simpkins N. S. Tetrahedron 2010, 66, 6585. doi: 10.1016/j.tet.2010.04.093
[36]	Peng T. F.; Liu T.; Zhao J. F.; Dong J. W.; Zhao Y. X.; Yang Y. X.; Yan X.; Xu W. L.; Shen X. F. J. Org. Chem. 2022, 83, 16743.
[37]	Song H. Q.; Song J. C.; Yan L. H.; He W. G.; Wang P. Y.; Xu Y. Z.; Wei H. B.; Xie W. Q. Tetrahedron Lett. 2021, 85, 153486. doi: 10.1016/j.tetlet.2021.153486
[38]	Wang Y.; Kong C.; Du Y.; Song H.; Zhang D.; Qin Y. Org. Biomol. Chem. 2012, 10, 2793. doi: 10.1039/c2ob00014h pmid: 22383065
[39]	Hakamata H.; Sato S.; Ueda H.; Tokuyama H. Org. Lett. 2017, 19, 5308. doi: 10.1021/acs.orglett.7b02602
[40]	Chen Z. G.; Zhong W.; Liu S. H.; Zou T.; Zhang K. Q.; Gong C. L.; Guo W. Y.; Kong F. Z.; Nie L. B.; Hu S. Q.; Wang H. F. Org. Lett. 2023, 25, 3391. doi: 10.1021/acs.orglett.3c00904
[41]	Yang J.; Singh B.; Cohen G.; Ting C. P. J. Am. Chem. Soc. 2023, 145, 19189. doi: 10.1021/jacs.3c07078
[42]	Xi Y.-K.; Zhang H. B.; Li R.-X.; Kang S.-Y.; Li J.; L Y. Chem.-Eur. J. 2019, 25, 3005. doi: 10.1002/chem.v25.12
[43]	Zhang B. X.; Zheng W. F.; Wang X. Q.; Sun D. Q.; Li C. Z. Angew. Chem., Int. Ed. 2016, 55, 1.
[44]	Hou Y.; Huo J. Y.; Li R. X.; Hou J.; Lei P.; Wei H. B.; Xie W. Q. Org. Lett. 2023, 25, 6949. doi: 10.1021/acs.orglett.3c02296 pmid: 37713279

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

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 21

References 44

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xiurong Wu, Chaojiang Xiao, Yi Shen, Hongxia Tang, Junyi Zhu, Bei Jiang. Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022 [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2764-2789.
[2]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[3]	Jingping Hu, Wenqing Chen, Yuyang Jiang, Jing Xu. Synthesis of Tetracyclic Core Structure of Daphnezomines A and B [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 171-177.
[4]	Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.
[5]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[6]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[7]	Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1557-1561.
[8]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[9]	Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.
[10]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[11]	Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.
[12]	Xifei Yan, Jianfeng Zheng, Wei-Dong Z. Li. Studies on the Chemical Synthesis of Natural Drugs Berberine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2217-2227.
[13]	Haixia Shi, Yaoyao Li, Jing Zhu, Haoxin Wang, Yuemao Shen. Discovery of Germicidin Glucuronides from Streptomyces sp. LZ35 [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2502-2506.
[14]	Ting Jiang, Hong Pu, Yanwen Duan, Xiaohui Yan, Yong Huang. New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020 [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1804-1820.
[15]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.