Citation: Yujie Dong, Jun Liu, Xing Gao, Ting Pan, Biming Mao, Songcheng Yu, Yongjun Wu, Cheng Zhang, Hongchao Guo. Pd-catalyzed cascade cyclization of allenylethylene carbonates and indandiones: Synthesis of tetracyclic dihydrocyclopentaindenofuranone derivatives^☆[J]. Chinese Chemical Letters, ;2023, 34(10): 108297. doi: 10.1016/j.cclet.2023.108297 shu

Pd-catalyzed cascade cyclization of allenylethylene carbonates and indandiones: Synthesis of tetracyclic dihydrocyclopentaindenofuranone derivatives^☆

Yujie Dong ^a ,
Jun Liu ^a ,
Xing Gao ^a ,
Ting Pan ^a ,
Biming Mao ^a ,
Songcheng Yu ^b ,
Yongjun Wu ^b ,
Cheng Zhang ^{a, *,} ,
Hongchao Guo ^{a, *,}

a.
Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, China
b.
College of Public Health, Zhengzhou University, Zhengzhou 450001, China

^☆

zhangc9711@cau.edu.cn

hchguo@cau.edu.cn

Received Date: 5 December 2022
Revised Date: 24 February 2023
Accepted Date: 1 March 2023
Available Online: 6 March 2023

Figures(5)

A palladium-catalyzed cascade cyclization of allenylethylene carbonates with 1,3-indandiones was developed, providing biologically interesting tetracyclic dihydrocyclopentaindenofuranone derivatives having three contiguous quaternary carbon centers in moderate to high yields with excellent diastereoselectivities. In this reaction, the allene moiety was fully fused into the cyclopentene ring.
- Palladium,
- Allenylethylene carbonates,
- Indandiones,
- Cascade cyclization,
- Decarboxylation
1. [1]
  T.K. Mohanta, Y. Tamboli, P.K. Zubaidha, Nat. Prod. Res. 28 (2014) 746–752. doi: 10.1080/14786419.2013.879303
2. [2]
  C. Sarkar, C. Quispe, S. Jamaddar, et al., Biomed. Pharmacother. 132 (2020) 110908. doi: 10.1016/j.biopha.2020.110908
3. [3]
  P.M. Manisha, S.M. Anuja, N.D. Prajakta, et al., GSC Biol. Pharm. Sci. 16 (2021) 229–240.
4. [4]
  J. Lu, L. Xie, K. Liu, et al., Phytother. Res. 35 (2021) 6114–6130. doi: 10.1002/ptr.7220
5. [5]
  T. Busch, A. Kirschning, Nat. Prod. Rep. 25 (2008) 318–341. doi: 10.1039/b705652b
6. [6]
  J.D. Weaver, A. Recio Ⅲ, A.J. Grenning, J.A. Tunge, Chem. Rev. 111 (2011) 1846–1913. doi: 10.1021/cr1002744
7. [7]
  A. Khan, Y.J. Zhang, Synlett 26 (2015) 853–860. doi: 10.1055/s-0034-1380170
8. [8]
  B.D.W. Allen, C.P. Lakeland, J.P.A. Harrity, Chem. Eur. J. 23 (2017) 13830–13857. doi: 10.1002/chem.201702486
9. [9]
  W.S. Guo, J.E. Gómez, À. Cristòfol, J.N. Xie, A.W. Kleij, Angew. Chem. Int. Ed. 57 (2018) 13735–13747. doi: 10.1002/anie.201805009
10. [10]
  N. De, E.J. Yoo, ACS Catal. 8 (2018) 48–58. doi: 10.1021/acscatal.7b03346
11. [11]
  L. Zuo, T. Liu, X. Chang, W. Guo, Molecules 24 (2019) 3930–3946. doi: 10.3390/molecules24213930
12. [12]
  J.E. Gómez, A.W. Kleij, Adv. Organomet. Chem. 71 (2019) 175–226.
13. [13]
  J. James, M. Jackson, P.J. Guiry, Adv. Synth. Catal. 361 (2019) 3016–3049. doi: 10.1002/adsc.201801575
14. [14]
  Q.Z. Li, Y. Liu, M.Z. Li, et al., Org. Biomol. Chem. 18 (2020) 3638–3648. doi: 10.1039/d0ob00458h
15. [15]
  B.M. Trost, G. Mata, Acc. Chem. Res. 53 (2020) 1293–1305. doi: 10.1021/acs.accounts.0c00152
16. [16]
  J. Wang, S.A. Blaszczyk, X. Li, W. Tang, Chem. Rev. 121 (2021) 110–139. doi: 10.1021/acs.chemrev.0c00160
17. [17]
  B. Niu, Y. Wei, M. Shi, Org. Chem. Front. 8 (2021) 3475–3501. doi: 10.1039/d1qo00273b
18. [18]
  B. Yan, W. Guo, Synthesis 54 (2022) 1964–1976. doi: 10.1055/a-1715-7413
19. [19]
  Y. You, Q. Li, Y.P. Zhang, et al., ChemCatChem 14 (2022) e202101887. doi: 10.1002/cctc.202101887
20. [20]
  M.M. Zhang, B.L. Qu, B. Shi, W.J. Xiao, L.Q. Lu, Chem. Soc. Rev. 51 (2022) 4146–4174. doi: 10.1039/d1cs00897h
21. [21]
  T. Pan, X. Gao, S. Yang, et al., Org. Lett. 23 (2021) 5750–5754. doi: 10.1021/acs.orglett.1c01921
22. [22]
  L. Li, P. Luo, Y. Deng, Z. Shao, Angew. Chem. Int. Ed. 58 (2019) 4710–4713. doi: 10.1002/anie.201901511
23. [23]
  J. Sun, J. Cao, Y. Han, C.G. Yan, Chin. J. Org. Chem. 40 (2020) 4122–4146. doi: 10.6023/cjoc202005003
24. [24]
  S. Asadi, G.M. Ziarani, Mol. Divers. 20 (2016) 111–152. doi: 10.1007/s11030-015-9589-z
1. [1]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
2. [2]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
3. [3]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
4. [4]
  Junlong Tang , Yuhan Zhao , Yangbin Jin , Liren Zhang , Yuanfang Wang , Wanqing Wu , Huanfeng Jiang . Palladium-catalyzed modular biomimetic synthesis of lignans derivatives. Chinese Chemical Letters, 2025, 36(7): 110969-. doi: 10.1016/j.cclet.2025.110969
5. [5]
  Zhao Gu , Yunhui Yang , Song Ye , Congyang Wang . 2,3-Arylacylation of allenes through synergetic catalysis of palladium and N-heterocyclic carbene. Chinese Chemical Letters, 2025, 36(5): 110334-. doi: 10.1016/j.cclet.2024.110334
6. [6]
  Peng Jin , Sili Lin , Dongmei Wang , Jinsong Fan , Qingyun Liu , Kun Li . Valence-band hybridization endows the reaction specificity of AgPd nanozyme for exclusive peroxidase mimicking and improved sensing performance. Chinese Chemical Letters, 2025, 36(11): 110916-. doi: 10.1016/j.cclet.2025.110916
7. [7]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
8. [8]
  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
9. [9]
  Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870
10. [10]
  Qian Liu , Yi Shi , Kaiya Wang , Xiao-Yu Hu . Tailoring cascade hydrolysis and cyclization efficiency in confined spaces via spatial and electrostatic regulation. Chinese Chemical Letters, 2025, 36(12): 111462-. doi: 10.1016/j.cclet.2025.111462
11. [11]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
12. [12]
  Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
13. [13]
  Yunqiang Li , Yongxian Huang , Sinuo Li , He Huang , Zhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051
14. [14]
  Junyou Ding , Xiaotong Li , Hongmin Lin , Bochao Ye , Xing Zhou , Feihu Cui , Yingming Pan , Haitao Tang . Highly regioselective hydrogermylation of unsaturated C-C bonds over ligand-control single atom palladium catalysts. Chinese Chemical Letters, 2025, 36(11): 111286-. doi: 10.1016/j.cclet.2025.111286
15. [15]
  Wenze Shi , Yang Dong , Xihong Wang , Min Wang , Jian Liao . SOP-ligand enabled palladium-catalyzed enantioselective anti-Markovnikov hydrothioesterification of α-substituted styrenes. Chinese Chemical Letters, 2025, 36(11): 111023-. doi: 10.1016/j.cclet.2025.111023
16. [16]
  Wenxiong Yu , Chenyu Yang , Xian Feng , Chengshuo Shen . Scholl cyclization of [6]helicenes into negatively curved hexa[7]circulenes. Chinese Chemical Letters, 2025, 36(11): 110939-. doi: 10.1016/j.cclet.2025.110939
17. [17]
  Jiang-Feng Xing , Kang Li , Wan Xiang , Yang-Yang Ju , Xin-Jing Zhao , Xiao-Hui Ma , Mei-Lin Zhang , Yuan-Zhi Tan . Oxa-helicenes embedding heptagons by stepwise cyclization of [6]helicene unit. Chinese Chemical Letters, 2025, 36(11): 110982-. doi: 10.1016/j.cclet.2025.110982
18. [18]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
19. [19]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
20. [20]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(916)
HTML views(25)

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

Pd-catalyzed cascade cyclization of allenylethylene carbonates and indandiones: Synthesis of tetracyclic dihydrocyclopentaindenofuranone derivatives☆

Metrics

通讯作者: 陈斌, bchen63@163.com

Pd-catalyzed cascade cyclization of allenylethylene carbonates and indandiones: Synthesis of tetracyclic dihydrocyclopentaindenofuranone derivatives^☆