Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1160-1180.DOI: 10.6023/cjoc202310009 Previous Articles Next Articles
REVIEWS
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,*()
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:
Tianfeng Penga, Yuxiang Zhaob, Shaojian Pua, Juan Luob, Teng Liub(), Yingchun Miaob(), Xianfu Shenb()
Received:
2023-10-08
Revised:
2023-11-10
Published:
2023-11-23
Contact:
E-mail: Supported by:
Share
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.
[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 |
[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. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||