Copper-Catalyzed Oxygenative Skeletal Rearrangement of Tetrahydro-β-carbolines Using H2O and O2 as Oxygen Sources
Yu-Sheng Peng
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
These authors contributed equally to this work.
Search for more papers by this authorWei Wang
National Key Laboratory of Green Pesticide, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, 550025 Guiyang, P. R. China
These authors contributed equally to this work.
Search for more papers by this authorJun Shi
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
These authors contributed equally to this work.
Search for more papers by this authorWei Wu
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorJun-Rong Song
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorWei-Dong Pan
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ge-Fei Hao
National Key Laboratory of Green Pesticide, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, 550025 Guiyang, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Hai Ren
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorYu-Sheng Peng
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
These authors contributed equally to this work.
Search for more papers by this authorWei Wang
National Key Laboratory of Green Pesticide, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, 550025 Guiyang, P. R. China
These authors contributed equally to this work.
Search for more papers by this authorJun Shi
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
These authors contributed equally to this work.
Search for more papers by this authorWei Wu
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorJun-Rong Song
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorWei-Dong Pan
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ge-Fei Hao
National Key Laboratory of Green Pesticide, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, 550025 Guiyang, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Hai Ren
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014 Guiyang, P. R. China
Natural Products Research Center of Guizhou Province, 550014 Guiyang, P. R. China
Search for more papers by this authorAbstract
Herein, we report an unprecedented skeletal rearrangement reaction of tetrahydro-β-carbolines enabled by copper-catalyzed single-electron oxidative oxygenation, in which H2O and O2 act as oxygen sources to generate a unique 2-hydroxyl-3-peroxide indoline intermediate. The synthetic reactivity of 2-hydroxyl-3-peroxide indoline species was demonstrated by a unique multi-step bond cleavage and formation cascade. Using a readily available copper catalyst under open-air conditions, highly important yet synthetically difficult spiro[pyrrolidone-(3,1-benzoxazine)] products were obtained in a single operation. The synthetic utility of this methodology is demonstrated by the efficient synthesis of the natural products donaxanine and chimonamidine, as well as the 3-hydroxyl-pyrroloindoline scaffold, in just one or two steps.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| ange202313687-sup-0001-2252376.cif169.8 KB | Supporting Information |
| ange202313687-sup-0001-2252388.cif347.9 KB | Supporting Information |
| ange202313687-sup-0001-2294682.cif237.7 KB | Supporting Information |
| ange202313687-sup-0001-misc_information.pdf17 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aV. U. Khuzhaev, S. F. Aripova, U. A. Abdullaev, Chem. Nat. Compd. 1995, 31, 610–611;
10.1007/BF01164890 Google Scholar
- 1bV. U. Rhuzhaev, B. Tashkhodzhaev, S. F. Aripova, Chem. Nat. Compd. 1995, 31, 604–606.
10.1007/BF01164889 Google Scholar
- 2
- 2aK. C. Nicolaou, A. Krasovskiy, V. E. Trepanier, D. Y. Chen, Angew. Chem. Int. Ed. 2008, 47, 4217–4220;
- 2bK. C. Nicolaou, A. Krasovskiy, U. Majumder, V. É. Trépanier, D. Y. K. Chen, J. Am. Chem. Soc. 2009, 131, 3690–3699;
- 2cP. Zhang, E. A. Terefenko, A. Fensome, Z. Zhang, Y. Zhu, J. Cohen, R. Winneker, J. Wrobel, J. Yardley, Bioorg. Med. Chem. Lett. 2002, 12, 787–790;
- 2dQ. Zhou, X. Song, X. Zhang, X. Fan, Org. Lett. 2022 24, 1280–1285;
- 2eI. Chatterjee, K. Ali, G. Panda, ChemMedChem 2023, 18, e202200617;
- 2fR. C. Rizzo, M. Udier-Blagović, D.-P. Wang, E. K. Watkins, M. B. Kroeger Smith, R. H. Smith, J. Tirado-Rives, W. L. Jorgensen, J. Med. Chem. 2002, 45, 2970–2987;
- 2gP. Zhang, E. A. Terefenko, A. Fensome, J. Wrobel, R. Winneker, S. Lundeen, K. B. Marschke, Z. Zhang, J. Med. Chem. 2002, 45, 4379–4382;
- 2hM. A. Collins, V. Hudak, R. Bender, A. Fensome, P. Zhang, L. Miller, R. C. Winneker, Z. Zhang, Y. Zhu, J. Cohen, R. J. Unwalla, J. Wrobel, Bioorg. Med. Chem. Lett. 2004, 14, 2185–2189;
- 2iT. Mizutani, S. Ishikawa, T. Nagase, H. Takahashi, T. Fujimura, T. Sasaki, A. Nagumo, K. Shimamura, Y. Miyamoto, H. Kitazawa, M. Kanesaka, R. Yoshimoto, K. Aragane, S. Tokita, N. Sato, J. Med. Chem. 2009, 52, 7289–7300.
- 3
- 3aJ. Braire, V. Dorcet, J. Vidal, C. Lalli, F. Carreaux, Org. Biomol. Chem. 2020, 18, 6042–6046;
- 3bG.-J. Mei, W. L. Koay, C. X. A. Tan, Y. Lu, Chem. Soc. Rev. 2021, 50, 5985–6012.
- 4
- 4aH. Takayama, Y. Matsuda, K. Masubuchi, A. Ishida, M. Kitajima, N. Aimi, Tetrahedron 2004, 60, 893–900;
- 4bU. V. Subba Reddy, M. Chennapuram, K. Seki, C. Seki, B. Anusha, E. Kwon, Y. Okuyama, K. Uwai, M. Tokiwa, M. Takeshita, H. Nakano, Eur. J. Org. Chem. 2017, 3874–3885;
- 4cP. Li, F. Yang, G. Hu, X. Zhang, J. Org. Chem. 2021, 86, 10360–10367;
- 4dA. A. Adhikari, J. D. Chisholm, Org. Lett. 2016, 18, 4100–4103;
- 4eK. Wu, Y. Du, Z. Wei, T. Wang, Chem. Commun. 2018, 54, 7443–7446;
- 4fS. D. Vaidya, N. P. Argade, Org. Lett. 2013, 15, 4006–4009;
- 4gA. Singh, G. P. Roth, Org. Lett. 2011, 13, 2118–2121.
- 5
- 5aK. Kobayashi, S. Fukamachi, D. Nakamura, O. Morikawa, H. Konishi, Heterocycles 2008, 75, 95–105;
- 5bT. Xiong, Y. Li, X. Bi, Y. Lv, Q. Zhang, Angew. Chem. Int. Ed. 2011, 50, 7140–7143;
- 5cY. Zhao, B. Huang, C. Yang, Q. Chen, W. Xia, Org. Lett. 2016, 18, 5572–5575;
- 5dE. Hernández, J. M. Vélez, C. P. Vlaar, Tetrahedron Lett. 2007, 48, 8972–8975;
- 5eY.-M. Yu, Y.-N. Huang, J. Deng, Org. Lett. 2017, 19, 1224–1227;
- 5fM. T. Richers, M. Breugst, A. Y. Platonova, A. Ullrich, A. Dieckmann, K. N. Houk, D. Seidel, J. Am. Chem. Soc. 2014, 136, 6123–6135;
- 5gC. González-Rodríguez, J. R. Suárez, J. A. Varela, C. Saá, Angew. Chem. Int. Ed. 2015, 54, 2724–2728;
- 5hS. Sun, C. Zhou, J.-T. Yu, J. Cheng, Org. Lett. 2019, 21, 6579–6583;
- 5iH. Fan, Y. Wan, P. Pan, W. Cai, S. Liu, C. Liu, Y. Zhang, Chem. Commun. 2020, 56, 86–89.
- 6
- 6aN. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 3871–3877;
- 6bN. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 1318–1320;
- 6cH. Zinnes, J. Jr. Shavel, J. Org. Chem. 1966, 31, 1765–1771.
- 7J. Ye, J. Wu, T. Lv, G. Wu, Y. Gao, H. Chen, Angew. Chem. Int. Ed. 2017, 56, 14968–14972.
- 8
- 8aM. Frahm, T. von Drathen, L. M. Gronbach, A. Voss, F. Lorenz, J. Bresien, A. Villinger, F. Hoffmann, M. Brasholz, Angew. Chem. Int. Ed. 2020, 59, 12450–12454;
- 8bL. M. Gronbach, A. Voss, M. Frahm, A. Villinger, J. Bresien, D. Michalik, M. Brasholz, Org. Lett. 2021, 23, 7834–7838;
- 8cM. Frahm, A. Voss, M. Brasholz, Chem. Commun. 2022, 58, 5467–5469.
- 9
- 9aS. Tadano, Y. Mukaeda, H. Ishikawa, Angew. Chem. Int. Ed. 2013, 52, 7990–7994;
- 9bK. Liang, X. Deng, X. Tong, D. Li, M. Ding, A. Zhou, C. Xia, Org. Lett. 2015, 17, 206–209;
- 9cY. Z. Cheng, Q. R. Zhao, X. Zhang, S. L. You, Angew. Chem. Int. Ed. 2019, 58, 18069–18074;
- 9dE. C. Gentry, L. J. Rono, M. E. Hale, R. Matsuura, R. R. Knowles, J. Am. Chem. Soc. 2018, 140, 3394–3402;
- 9eJ. Wu, Y. Dou, R. Guillot, C. Kouklovsky, G. Vincent, J. Am. Chem. Soc. 2019, 141, 2832–2837;
- 9fK. Liu, W. Song, Y. Deng, H. Yang, C. Song, T. Abdelilah, S. Wang, H. Cong, S. Tang, A. Lei, Nat. Commun. 2020, 11, 3;
- 9gX. Liu, D. Yang, Z. Liu, Y. Wang, Y. Liu, S. Wang, P. Wang, H. Cong, Y.-H. Chen, L. Lu, X. Qi, H. Yi, A. Lei, J. Am. Chem. Soc. 2023, 145, 3175–3186;
- 9hA. Y. Ji, A. Thirupathi, J. Y. Hwang, Y. Kim, G. Han, K.-H. Ahn, K. Kang, E. J. Kang, Org. Lett. 2023, 25, 1541–1546;
- 9iW.-Y. Zhang, H.-C. Wang, Y. Wang, C. Zheng, S.-L. You, J. Am. Chem. Soc. 2023, 145, 10314–10321;
- 9jL. Li, X.-M. Chen, Z.-S. Wang, B. Zhou, X. Liu, X. Lu, L.-W. Ye, ACS Catal. 2017, 7, 4004–4010.
- 10
- 10aS.-Y. Jiang, J. Shi, W. Wang, Y.-Z. Sun, W. Wu, J.-R. Song, X. Yang, G.-F. Hao, W.-D. Pan, H. Ren, ACS Catal. 2023, 13, 3085–3092;
- 10bH. Ren, Y.-A. Wu, J.-R. Song, W. Wu, X. Yang, J. Shi, W.-D. Pan, Org. Chem. Front. 2023, 10, 774–779;
- 10cW. Wang, S.-Y. Jiang, J.-R. Song, W. Wu, J. Shi, Z.-Y. Li, Y.-A. Wu, Q. Chi, W.-D. Pan, H. Ren, Org. Lett. 2022. 24, 2716–2721;
- 10dJ. Shi, R.-A. Wang, W. Wu, J.-R. Song, Q. Chi, W.-D. Pan, H. Ren, Org. Lett. 2022, 24, 3358–3362;
- 10eZ.-Y. Li, W. Wang, J.-R. Song, R.-A. Wang, J. Shi, Q. Chi, Y. Li, H. Ren, W.-D. Pan, J. Org. Chem. 2021, 86, 17164–17172;
- 10fH. Ren, J. R. Song, Z. Y. Li, W. D. Pan, Org. Lett. 2019, 21, 6774–6778.
- 11
- 11aN. Gulzar, M. Klussmann, Org. Biomol. Chem. 2013, 11, 4516–4520;
- 11bJ. Ye, Y. Lin, Q. Liu, D. Xu, F. Wu, B. Liu, Y. Gao, H. Chen, Org. Lett. 2018, 20, 5457–5460;
- 11cH. Chen, F. Ye, J. Luo, Y. Gao, Org. Lett. 2019, 21, 7475–7477;
- 11dT. von Drathen, F. Hoffmann, M. Brasholz, Chem. Eur. J. 2018, 24, 10253–10259.
- 12Deposition number 2272170 (2 a) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
- 13Deposition number 2252376 (2 c) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
- 14Deposition number 2252388 (5) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
- 15
- 15aM. Masarwa, H. Cohen, D. Meyerstein, D. L. Hickman, A. Bakac, J. H. Espenson, J. Am. Chem. Soc. 1988, 110, 4293–4297;
- 15bC. Tang, X. Qiu, Z. Cheng, N. Jiao, Chem. Soc. Rev. 2021, 50, 8067–8101.
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
