Citation: Meng Zhaoxiang, Mi Fen, Lu Fei, Tan Wei, Liu Xiao-Yu, Qin Yong. Assembly of the 6/3/5/6 tetracyclic core of rearranged-type C₁₉-diterpenoid alkaloids[J]. Chinese Chemical Letters, ;2020, 31(7): 1903-1905. doi: 10.1016/j.cclet.2020.01.043 shu

Assembly of the 6/3/5/6 tetracyclic core of rearranged-type C₁₉-diterpenoid alkaloids

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

xyliu@scu.edu.cn

yongqin@scu.edu.cn

Received Date: 23 December 2019
Revised Date: 8 January 2020
Accepted Date: 19 January 2020
Available Online: 20 January 2020

Figures(4)

A synthetic study toward the structurally complex rearranged-type C₁₉-diterpenoid alkaloids leading to construction of the strained 6/3/5/6 tetracyclic core is presented. The synthesis features an intramolecular Diels-Alder cycloaddition reaction to assemble the highly substituted central cyclopropane motif, which may serve as a key strategy for the total synthesis of relevant natural product molecules.
- Diterpenoid alkaloid,
- Diels-Alder cycloaddition,
- Cyclopropane,
- Natural product,
- Total synthesis
1. [1]
  (a) F.P. Wang, Q.H. Chen, The C19-diterpenoid alkaloids, in:G.A. Cordell (Ed.), The Alkaloids:Chemistryand Biology, 69, Elsevier Science, New York,2010,pp.1-577;
  (b) F.P. Wang, Q.H. Chen, X.Y. Liu, Nat. Prod. Rep. 27 (2010) 529-570.
2. [2]
  K. Wiesner, M. Götz, D.L. Simmons, et al., Tetrahedron Lett. 1 (1959) 15-24.
3. [3]
  J. Xiong, N.H. Tan, C.J. Ji, Y. Lu, N.B. Gong, Tetrahedron Lett. 49 (2008) 4851-4853. doi: 10.1016/j.tetlet.2008.06.008
4. [4]
  (a) Y. Shen, H.L. Ai, T.W. Cao, et al., Helv. Chim. Acta 95 (2012) 509-513;
  (b) T.P. Yin, L. Cai, H.X. Fang, et al., Phytochemistry 116 (2015) 314-319.
5. [5]
  (a) E.C. Cherney, P.S. Baran, Isr. J. Chem. 51 (2011) 391-405;
  (b) A.M. Hamlin, J.K. Kisunzu, R. Sarpong, Org. Biomol. Chem. 12 (2014) 1846-1860;
  (c) X.Y. Liu, Y. Qin, Asian J. Org. Chem. 4 (2015) 1010-1019;
  (d) G. Zhu, R. Liu, B. Liu, Synthesis 47 (2015) 2691-2708;
  (e) X.Y. Liu, Y. Qin, Nat. Prod. Rep. 34 (2017) 1044-1050;
  (f) C. Dank, R. Sanichar, K.L. Choo, M. Olsen, M. Lautens, Synthesis 51 (2019)3915-3946.
6. [6]
  (a) K. Wiesner, T.Y.R. Tsai, K. Huber, S.E. Bolton, R. Vlahov, J. Am. Chem. Soc. 96(1974) 4990-4992;
  (b) K. Wiesner, T.Y.R. Tsai, K.P. Nambiar, Can. J. Chem. 56 (1978) 1451-1454;
  (c) K. Wiesner, Pure Appl. Chem. 51 (1979) 689-703.
7. [7]
  Y. Shi, J.T. Wilmot, L.U. Nordstrøm, D.S. Tan, D.Y. Gin, J. Am. Chem. Soc. 135(2013) 14313-14320. doi: 10.1021/ja4064958
8. [8]
  (a) C.J. Marth, G.M. Gallego, J.C. Lee, et al., Nature 528 (2015) 493-498;
  (b) K.G.M. Kou, S. Kulyk, C.J. Marth, et al., J. Am. Chem. Soc. 139 (2017) 13882-13896.
9. [9]
  (a) Y. Nishiyama, S. Yokoshima, T. Fukuyama, Org. Lett. 18 (2016) 2359-2362;
  (b) Y. Nishiyama, S. Yokoshima, T. Fukuyama, Org. Lett. 19 (2017) 5833-5835.
10. [10]
  D. Kamakura, H. Todoroki, D. Urabe, K. Hagiwara, M. Inoue, Angew. Chem. Int.Ed. 59 (2020) 479-486. doi: 10.1002/anie.201912737
11. [11]
  (a) D. Barker, M.A. Brimble, M.D. McLeod, G.P. Savage, Org. Biomol. Chem. 2(2004) 1659-1669;
  (b) D.F. Taber, J.L. Liang, B. Chen, L. Cai, J. Org. Chem. 70 (2005) 8739-8742;
  (c) R.M. Conrad, J. Du Bois, Org. Lett. 9 (2007) 5465-5468;
  (d) Z.G. Liu, H. Cheng, M.J. Ge, L. Xu, F.P. Wang, Tetrahedron 69 (2013) 5431-5437;
  (e) H. Cheng, F.H. Zeng, D. Ma, et al., Org. Lett. 16 (2014) 2299-2301;
  (f) K. Hagiwara, T. Tabuchi, D. Urabe, M. Inoue, Chem. Sci. 7 (2016) 4372-4378;
  (g) T. Tabuchi, D. Urabe, M. Inoue, J. Org. Chem. 81 (2016) 10204-10213;
  (h) K. Minagawa, D. Urabe, M. Inoue, J. Antibiot. 71 (2018) 326-332;
  (i) Z. Lv, L. Gao, C. Cheng, et al., Chem. -Asian J. 13 (2018) 955-958;
  (j) M. Liu, C. Cheng, W. Xiong, et al., Org. Chem. Front. 5 (2018) 1502-1505;
  (k) N.A. Doering, K.G.M. Kou, K. Norseeda, et al., J. Org. Chem. 83 (2018) 12911-12920;
  (l) X.H. Zhou, Y. Liu, R.J. Zhou, et al., Chem. Commun. 54 (2018) 12258-12261;
  (m) R.J. Zhou, G.Y. Dai, X.H. Zhou, et al., Org. Chem. Front. 6 (2019) 377-382.
12. [12]
  C. Ebner, E.M. Carreira, Chem. Rev. 117 (2017) 11651-11679. doi: 10.1021/acs.chemrev.6b00798
13. [13]
  (a) J. Gong, H. Chen, X.Y. Liu, et al., Nat. Commun. 7 (2016) 12183;
  (b) X.H. Li, M. Zhu, Z.X. Wang, et al., Angew. Chem. Int. Ed. 55 (2016) 15667-15671;
  (c) W. Nie, J. Gong, Z. Chen, et al., J. Am. Chem. Soc. 141 (2019) 9712-9718.
14. [14]
  (a) J. Zsindely, H. Schmid, Helv. Chim. Acta 51 (1968) 1510-1514;
  (b) T. Imagawa, M. Kawanisi, K. Sisido, J. Chem. Soc. Dalton Trans. (1971) 1292-1293;
  (c) P. Heimbach, K.J. Ploner, F. Thömel, Angew. Chem. Int. Ed. 10 (1971) 276-277;
  (d) E.N. Marvell, J. Seubert, G. Vogt, G. Zimmer, G. Moy, J.R. Siegmann,Tetrahedron 34 (1978) 1307-1322;
  (e) T. Imagawa, T. Nakagawa, M. Kawanisi, K. Sisido, Bull. Chem. Soc. Jpn. 52(1979) 1506-1510;
  (f) P. Loeliger, H. Mayer, Helv. Chim. Acta 63 (1980) 1604-1608;
  (g) H. Jendralla, K. Jelich, G. DeLucca, L.A. Paquette, J. Am. Chem. Soc.108 (1986)3731-3739;
  (h) G. Maier, N.H. Wiegand, S. Baum, et al., Chem. Ber. 122 (1989) 767-779;
  (i) R. ten Have, A.M. van Leusen, Tetrahedron 54 (1998) 1913-1920;
  (j) S.M. Ng, C.M. Beaudry, D. Trauner, Org. Lett. 5 (2003) 1701-1704;
  (k) J.E. Moses, J.E. Baldwin, R.M. Adlington, A.R. Cowley, R. Marquez,Tetrahedron Lett. 44 (2003) 6625-6627;
  (l) K.S. Khuong, C.M. Beaudry, D. Trauner, K.N. Houk, J. Am. Chem. Soc. 127(2005) 3688-3689;
  (m) J. Dubarle-Offner, J. Marrot, M.N. Rager, F.L. Bideau, G. Jaouen, Synlett(2007) 800-802;
  (n) K.C. Gue'rard, A. Gue'rinot, C. Bouchard-Aubin, et al., J. Org. Chem. 77 (2012)2121-2133;
  (o) C.C. Tseng, H. Ding, A. Li, Y. Guan, D.Y.K. Chen, Org. Lett. 13 (2011) 4410-4413;
  (p) M.J.R. Richter, M. Schneider, M. Brandstätter, E.M. Carreira, J. Am. Chem.Soc. 140 (2018) 16704-16710;
  (q) L.A. Wein, K. Wurst, P. Angyal, L. Weisheit, T. Magauer, J. Am. Chem. Soc.141(2019) 19589-19593.
15. [15]
  M. Boumediene, R.F. Guignard, S.Z. Zard, Tetrahedron 72 (2016) 3678-3686. doi: 10.1016/j.tet.2016.03.032
16. [16]
  . Van Rheenen, Tetrahedron Lett. 10 (1969) 985-988. doi: 10.1016/S0040-4039(01)97716-0
1. [1]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
2. [2]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
3. [3]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
4. [4]
  Qunlong Zhang , Jingyi Kang , Jingwen Wang , Tiancheng Tan , Zhaoyong Lu . Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G. Chinese Chemical Letters, 2025, 36(3): 109915-. doi: 10.1016/j.cclet.2024.109915
5. [5]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
6. [6]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
7. [7]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
8. [8]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
9. [9]
  Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
10. [10]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
11. [11]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
12. [12]
  Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
13. [13]
  Yingjie Wang , Peng Tang , Wenchao Tu , Qi Gao , Cuizhu Wang , Luying Tan , Lixin Zhao , Hongye Han , Liefeng Ma , Kouharu Otsuki , Weilie Xiao , Wenli Wang , Jinping Liu , Yong Li , Zhajun Zhan , Wei Li , Xianli Zhou , Ning Li . Highly anticipated natural diterpenoids as an important source of new drugs in 2013–2023. Chinese Chemical Letters, 2025, 36(1): 109955-. doi: 10.1016/j.cclet.2024.109955
14. [14]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
15. [15]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
16. [16]
  Ying Gao , Rong Zhou , Qiwen Wang , Shaolong Qi , Yuanyuan Lv , Shuang Liu , Jie Shen , Guocan Yu . Natural killer cell membrane doped supramolecular nanoplatform with immuno-modulatory functions for immuno-enhanced tumor phototherapy. Chinese Chemical Letters, 2024, 35(10): 109521-. doi: 10.1016/j.cclet.2024.109521
17. [17]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
18. [18]
  Haobo Wang , Fei Wang , Yong Liu , Zhongxiu Liu , Yingjie Miao , Wanhong Zhang , Guangxin Wang , Jiangtao Ji , Qiaobao Zhang . Emerging natural clay-based materials for stable and dendrite-free lithium metal anodes: A review. Chinese Chemical Letters, 2025, 36(2): 109589-. doi: 10.1016/j.cclet.2024.109589
19. [19]
  Zhexin Chen , Yuqing Shi , Fang Zhong , Kai Zhang , Furong Zhang , Shenghong Xie , Zhongbin Cheng , Qian Zhou , Yi-You Huang , Hai-Bin Luo . Discovery of amentoflavone as a natural PDE4 inhibitor with anti-fibrotic effects. Chinese Chemical Letters, 2025, 36(4): 109956-. doi: 10.1016/j.cclet.2024.109956
20. [20]
  Zirui Zhu , Peng Liu , Jinhua Wang , Hongbin Zhang , Wei Luo . Effects of nano-metakaolin on the enhanced properties and microstructure development of natural hydraulic lime. Chinese Chemical Letters, 2025, 36(4): 109794-. doi: 10.1016/j.cclet.2024.109794

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(746)
HTML views(61)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Assembly of the 6/3/5/6 tetracyclic core of rearranged-type C19-diterpenoid alkaloids

Metrics

通讯作者: 陈斌, bchen63@163.com

Assembly of the 6/3/5/6 tetracyclic core of rearranged-type C₁₉-diterpenoid alkaloids