Citation: Jindian Duan, Xiaojuan Ding, Pui Ying Choy, Binyan Xu, Luchao Li, Hong Qin, Zheng Fang, Fuk Yee Kwong, Kai Guo. Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway[J]. Chinese Chemical Letters, ;2024, 35(10): 109565. doi: 10.1016/j.cclet.2024.109565 shu

Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway

Jindian Duan ^a ,
Xiaojuan Ding ^a ,
Pui Ying Choy ^b ,
Binyan Xu ^a ,
Luchao Li ^a ,
Hong Qin ^a ,
Zheng Fang ^a ,
Fuk Yee Kwong ^{b, *,} ,
Kai Guo ^{a, *,}

a.
College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 211816, China
b.
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Hong Kong, China

fykwong@cuhk.edu.hk

guok@njtech.edu.cn

Received Date: 5 September 2023
Revised Date: 18 January 2024
Accepted Date: 28 January 2024
Available Online: 1 February 2024

Figures(5)

An oxidative annulation of 2-arylidene-1,3-indanediones with Meldrum's acid has been developed for the divergent syntheses of spirolactones with a spirocenter located at the γ-position with respect to the carbonyl group. This heteroannulation protocol tolerates various functional groups and delivers moderate-to-good product yields. Interestingly, the reaction outcomes are exclusively controlled by the reaction oxidant/medium. This annulation strategy can also be executed in the flow system with decent product yields. Control experiments revealed that the reaction proceeds via a radical tandem annulation pathway.
- Spirolactonisation,
- γ-Spirolactones,
- 2-Arylidene-1,3-indanediones,
- Meldrum's acid,
- Divergent synthesis
1. [1]
  A. Bartoli, F. Rodier, L. Commeiras, J. Parrain, G. Chouraqui, Nat. Prod. Rep. 28 (2011) 763–782. doi: 10.1039/c0np00053a
2. [2]
  A. Quintavalla, Curr. Med. Chem. 25 (2018) 917–962. doi: 10.2174/0929867324666171106162259
3. [3]
  P. Liu, S. Hong, S.M. Weinreb, J. Am. Chem. Soc. 130 (2008) 7562–7563. doi: 10.1021/ja802700z
4. [4]
  Y. Fan, H. Zhang, Y. Zhou, et al., J. Am. Chem. Soc. 137 (2015) 138–141. doi: 10.1021/ja511813g
5. [5]
  S.S. Thorat, M.N. Palange, R. Kontham, ACS Omega 3 (2018) 7036–7045. doi: 10.1021/acsomega.8b00701
6. [6]
  C.M. Marson, Chem. Soc. Rev. 40 (2011) 5514–5533. doi: 10.1039/c1cs15119c
7. [7]
  K. Hiesinger, D. Dar'in, E. Proschak, M. Krasavin, J. Med. Chem. 64 (2021) 150–183. doi: 10.1021/acs.jmedchem.0c01473
8. [8]
  B. Bister, D. Bischoff, M. Ströbele, et al., Angew. Chem. Int. Ed. 43 (2004) 2574–2576. doi: 10.1002/anie.200353160
9. [9]
  A.M. Sherwood, R.S. Crowley, K.F. Paton, et al., J. Med. Chem. 60 (2017) 3866–3878. doi: 10.1021/acs.jmedchem.7b00148
10. [10]
  T.Z. Li, X.T. Yang, J.P. Wang, et al., Org. Lett. 23 (2021) 8380–8384. doi: 10.1021/acs.orglett.1c03120
11. [11]
  S. Rodriguez, P. Wipf, Synthesis 17 (2004) 2767–2783.
12. [12]
  W.T. Wu, L. Zhang, S.L. You, Chem. Soc. Rev. 45 (2016) 1570–1580. doi: 10.1039/C5CS00356C
13. [13]
  A. Yoshimura, V.V. Zhdankin, Chem. Rev. 116 (2016) 3328–3435. doi: 10.1021/acs.chemrev.5b00547
14. [14]
  R. Kumar, F.V. Singh, N. Takenaga, T. Dohi, Chem. Asian J. 17 (2022) e202101115. doi: 10.1002/asia.202101115
15. [15]
  M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. Int. Ed. 49 (2010) 2175–2177. doi: 10.1002/anie.200907352
16. [16]
  M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. Int. Ed. 52 (2013) 9215–9218. doi: 10.1002/anie.201303559
17. [17]
  T. Dohi, N. Takenaga, T. Nakae, et al., J. Am. Chem. Soc. 135 (2013) 4558–4566. doi: 10.1021/ja401074u
18. [18]
  C. Hempel, C. Maichle-Mössmer, M.A. Pericàsc, B.J. Nachtsheim, Adv. Synth. Catal. 359 (2017) 2931–2941. doi: 10.1002/adsc.201700246
19. [19]
  T. Dohi, H. Sasa, K. Miyazaki, et al., J. Org. Chem. 82 (2017) 11954–11960. doi: 10.1021/acs.joc.7b02037
20. [20]
  H. Li, E. Subbotina, A. Bunrit, F. Wang, J.S.M. Samec, Chem. Sci. 10 (2019) 3681–3686. doi: 10.1039/C8SC05476B
21. [21]
  M. Uyanik, T. Kato, N. Sahara, O. Katade, K. Ishihara, ACS Catal. 9 (2019) 11619–11626. doi: 10.1021/acscatal.9b04322
22. [22]
  C. Zhang, F. Bu, C. Zeng, et al., CCS Chem. 4 (2022) 1199–1207. doi: 10.31635/ccschem.021.202100860
23. [23]
  Y. Liu, X. Zhang, R. Zeng, et al., Molecules 22 (2017) 1882. doi: 10.3390/molecules22111882
24. [24]
  J.L. Li, B. Sahoo, C.G. Daniliuc, F. Glorius, Angew. Chem. Int. Ed. 53 (2014) 10515–10519. doi: 10.1002/anie.201405178
25. [25]
  Y. Gao, Y. Ma, C. Xu, et al., Adv. Synth. Catal. 360 (2018) 479–484. doi: 10.1002/adsc.201701413
26. [26]
  H. Zhang, Q. Ma, D. Liu, X. Hui, Chem. Commun. 55 (2019) 298–301. doi: 10.1039/C8CC08578A
27. [27]
  Y. Gao, D. Liu, Z. Fu, W. Huang, Org. Lett. 21 (2019) 926–930. doi: 10.1021/acs.orglett.8b03892
28. [28]
  Y. Mostinski, D. Lankri, D. Tsvelikhovsky, Synthesis 49 (2017) 2361–2373. doi: 10.1055/s-0036-1588783
29. [29]
  Q. Deng, H. Wadepohl, L.H. Gade, J. Am. Chem. Soc. 134 (2012) 2946–2949. doi: 10.1021/ja211859w
30. [30]
  Y. Qiu, B. Yang, T. Jiang, C. Zhu, J.E. Bäckvall, Angew. Chem. Int. Ed. 56 (2017) 3221–3225. doi: 10.1002/anie.201612384
31. [31]
  N.A. Weires, Y. Slutskyy, L.E. Overman, Angew. Chem. Int. Ed. 58 (2019) 8561–8565. doi: 10.1002/anie.201903353
32. [32]
  B. Lin, T. Yang, D. Zhang, et al., Angew. Chem. Int. Ed. 61 (2022) e202201739. doi: 10.1002/anie.202201739
33. [33]
  S. Sternativo, A. Calandriello, F. Costantino, et al., Angew. Chem. Int. Ed. 50 (2011) 9382–9385. doi: 10.1002/anie.201104819
34. [34]
  B. Cui, J. Zuo, J. Zhao, et al., J. Org. Chem. 79 (2014) 5305–5314. doi: 10.1021/jo500432c
35. [35]
  J. Cao, S. Dong, D. Jiang, et al., J. Org. Chem. 82 (2017) 4186–4193. doi: 10.1021/acs.joc.7b00153
36. [36]
  X. Sun, M. Zhou, J. Zhu, et al., Org. Chem. Front. 9 (2022) 2316–2321. doi: 10.1039/D1QO01952J
37. [37]
  E.L. McInturff, J. Mowat, A.R. Waldeck, M.J. Krische, J. Am. Chem. Soc. 135 (2013) 17230–17235. doi: 10.1021/ja410533y
38. [38]
  P. Šafář, Š. Marchalín, M. Šoral, J. Moncol, A. Daïch, Org. Lett. 19 (2017) 4742–4745. doi: 10.1021/acs.orglett.7b01881
39. [39]
  M.M. Liu, X.C. Yang, Y.Z. Hua, J.B. Chang, M.C. Wang, Org. Lett. 21 (2019) 7089–7093. doi: 10.1021/acs.orglett.9b02658
40. [40]
  M. Tobisu, N. Chatani, T. Asaumi, et al., J. Am. Chem. Soc. 122 (2000) 12663–12674. doi: 10.1021/ja003018i
41. [41]
  K.Y. Lee, D.Y. Park, J.N. Kim, Bull. Korean Chem. Soc. 27 (2006) 1489–1492. doi: 10.5012/bkcs.2006.27.9.1489
42. [42]
  Q. Wu, L. Li, B. Xu, et al., Green Synth. Catal. 4 (2023) 150–153. doi: 10.1016/j.gresc.2023.01.001
43. [43]
  G. Xu, C. Jia, X. Wang, et al., Org. Lett. 24 (2022) 1060–1065. doi: 10.1021/acs.orglett.1c04308
44. [44]
  J. Duan, G. Xu, B. Rong, et al., Green Synth. Catal. 2 (2021) 237–240. doi: 10.1016/j.gresc.2021.03.001
45. [45]
  S. Zhang, G. Xu, H. Yan, et al., Chin. Chem. Lett. 33 (2022) 5128–5131. doi: 10.1016/j.cclet.2022.04.006
46. [46]
  M. Li, F.Y. Kwong, Angew. Chem. Int. Ed. 57 (2018) 6512–6516. doi: 10.1002/anie.201801706
47. [47]
  T. Liu, K.B. Gan, R.L. Zhong, X. He, F.Y. Kwong, Org. Lett. 24 (2022) 6805–6809. doi: 10.1021/acs.orglett.2c02728
48. [48]
  X. He, R. Li, P.Y. Choy, et al., Chem. Sci. 13 (2022) 13617–13622. doi: 10.1039/D2SC04431E
49. [49]
  P.Y. Yeung, K.H. Chung, F.Y. Kwong, Org. Lett. 13 (2011) 2912–2915. doi: 10.1021/ol2009522
50. [50]
  M.B. Plutschack, B. Pieber, K. Gilmore, P.H. Seeberger, Chem. Rev. 117 (2017) 11796–11893. doi: 10.1021/acs.chemrev.7b00183
51. [51]
  C.A. Hone, C.O. Kappe, Chem. Methods 1 (2021) 454–467. doi: 10.1002/cmtd.202100059
52. [52]
  W.C. Fu, P.M. MacQueen, T.F. Jamison, Chem. Soc. Rev. 50 (2021) 7378–7394. doi: 10.1039/D0CS00670J
53. [53]
  A.S. Ivanov, Chem. Soc. Rev. 37 (2008) 789–811. doi: 10.1039/b716020h
54. [54]
  S. Manna, A.P. Antonchick, Angew. Chem. Int. Ed. 54 (2015) 14845–14848. doi: 10.1002/anie.201502872
1. [1]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
2. [2]
  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
3. [3]
  Pei Xu , Tian-Zi Hao , Zhi-Tao Liu , Yi-Qin Liu , Hui-Xian Jiang , Dong Guo , Xu Zhu . Visible-light-induced dual catalysis for divergent reduction of nitro compounds with CO₂ radical anion. Chinese Chemical Letters, 2025, 36(10): 110899-. doi: 10.1016/j.cclet.2025.110899
4. [4]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
5. [5]
  Yiwen Xu , Chaozheng He , Chenxu Zhao , Ling Fu . Single-atom Ti doping on S-vacancy two-dimensional CrS₂ as a catalyst for ammonia synthesis: A DFT study. Chinese Chemical Letters, 2025, 36(4): 109797-. doi: 10.1016/j.cclet.2024.109797
6. [6]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
7. [7]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
8. [8]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
9. [9]
  Ze-Yuan Ma , Mei Xiao , Cheng-Kun Li , Adedamola Shoberu , Jian-Ping Zou . S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076
10. [10]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
11. [11]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
12. [12]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
13. [13]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
14. [14]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
15. [15]
  Nana Yang , Rui Yuan , Xinyue Fu , Xiao Tian , Jin Yu , Shengzhou Ma , Liuqing Wen , Jiabin Zhang . Concise synthesis of NDP-activated uronic acid by an oxidation reaction insertion strategy. Chinese Chemical Letters, 2025, 36(8): 110757-. doi: 10.1016/j.cclet.2024.110757
16. [16]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
17. [17]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
18. [18]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
19. [19]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
20. [20]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1093)
HTML views(42)

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