Chinese Journal of Organic Chemistry >
Research Progress on the Synthetic Methods of Pancratistatin
Received date: 2023-11-28
Revised date: 2024-01-12
Online published: 2024-03-05
Supported by
National Natural Science Foundation of China(2104044); Yunnan Fundamental Research Projects(202201AS070086); Yunnan Provincial Science and Technology Department-Kunming Medical University Applied Basic Research Joint Special Fund Project(202201AY070001-003); Yunnan Provincial Science and Technology Department-Kunming Medical University Applied Basic Research Joint Special Fund Project(202101AY070001-041); Yunnan Academician Expert Workstation(202305AF150054); Open Fund of Yunnan Key Laboratory of Pharmacology for Natural Products(YKLPNP-G2305)
Pancratistatin is a natural alkaloid with prominent antitumor activity. Structurally, pancratistatin has an isocarbostyril core skeleton, fused with a highly oxygenated cyclohexane ring, with six consecutive stereogenic centers. Regioselective introduction of substituted aromatic ring into the core structure, construction of the lactam ring, and control of stereocenters are major challenges in the synthesis of pancratistatin. The preliminary synthetic work of pancratistatin and the research progresses of its total synthesis since 2000 are summarized, and the synthetic strategies and key steps during the total synthesis are illustrated.
Key words: pancratistatin; racemic synthesis; asymmetric synthesis
Leilei Liang , Jiacan Yao , Fan Ding , Chang Xu , Dandan Liu . Research Progress on the Synthetic Methods of Pancratistatin[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1793 -1810 . DOI: 10.6023/cjoc202309023
| [1] | Hartwell, J. L. Lloydia 1971, 30, 379. |
| [2] | Ma, N.; Chen, N.; Ji, Y. Heilongjiang Med. J. 2023, 26, 205. |
| [3] | Pettit, G. R.; Gaddamidi, V.; Cragg, G. M. J. Nat. Prod. 1984, 47, 1018. |
| [4] | Pettit, G. R.; Pettit III, G. R.; Backhaus, R. A.; Boyd, M. R.; Meerow, A. W. J. Nat. Prod. 1993, 56, 1682. |
| [5] | NCI database. Available at: http://dtp.nci.nih.gov/. |
| [6] | (a) Gabrielsen, B.; Montath, T. P.; Huggins, J. W.; Kefauver, D. F.; Pettit, G. R.; Groszek, G.; Hollingshead, M.; Kirsi, J. J.; Shannon, W. M.; Schubert, E. M.; Dare, J.; Ugarkar, B.; Ussery, M. A.; Phelan, M. J. J. Nat. Prod. 1992, 55, 1569. |
| [6] | (b) Ouarzane-Amara, M.; Franetich, J. F.; Mazier, D.; Pettit, G. R.; Meijer, L.; Doerig, C.; Desportes-Livage, I. Antimicrob. Agents Chemother. 2001, 45, 3409. |
| [7] | (a) Kornienko, A.; Evidente, A. Chem. Rev. 2008, 108, 1982. |
| [7] | (b) Wang, P. P.; Yang, C. S.; Li, X. D.; Jiang, Y. G.; Yan, X.; Zhou, Z. H. Chin. J. Org. Chem. 2018, 38, 2199. |
| [7] | (王平平, 杨成帅, 李晓东, 蒋雨果, 严兴, 周志华, 有机化学, 2018, 38, 2199.) |
| [8] | Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. |
| [9] | Tian, X. R.; Hudlicky, T.; Konigsberger, K. J. Am. Chem. Soc. 1995, 117, 3643. |
| [10] | Rinner, U.; Hudlicky, T. Synlett 2005, 3, 365. |
| [11] | Manpadi, M.; Kornienko, A. Org. Prep. Proced. Int. 2008, 40, 107. |
| [12] | (a) Kim, S.; Ko, H.; Kim, E.; Kim, D. Org. Lett. 2002, 4, 1343. |
| [12] | (b) Ko, H.; Kim, E.; Park, J. E.; Kim, D.; Kim, S. J. Org. Chem. 2004, 69, 112. |
| [13] | Jung, Y. G.; Kang, H. U.; Cho, H. K.; Cho, C. G. Org. Lett. 2011, 21, 5890. |
| [14] | Cho, H. K.; Lim, H. Y.; Cho, C. G. Org. Lett. 2013, 22, 5806 |
| [15] | Rigby, J. H.; Maharoof, U. S. M.; Mateo, M. E. J. Am. Chem. Soc. 2000, 122, 6624. |
| [16] | Pettit, G. R.; Melody, N.; Herald, D. L. J. Org. Chem. 2001, 66, 2583. |
| [17] | Li, M.; Wu, A. M.; Zhou, P. J. Tetrahedron Lett. 2006, 47, 3707. |
| [18] | Dam, J. H.; Madsen, R. Eur. J. Org. Chem. 2009, 27, 4666. |
| [19] | Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444. |
| [20] | Cagide-Fagín, F.; Nieto-García, O.; Lago-Santomé, H.; Alonso, R. J. Org. Chem. 2012, 77, 11377. |
| [21] | Akai, S.; Kojima, M.; Yamauchi, S.; Kohji, T.; Nakamura, Y.; Sato, K. Asian J. Org. Chem. 2013, 2, 299. |
| [22] | Potter, T. J.; Ellman, J. A. Org. Lett. 2017, 19, 2985. |
| [23] | Hernandez, L. W.; Pospech, J.; Kl?ckner, U.; Bingham, T. W.; Sarlah, D. J. Am. Chem. Soc. 2017, 139, 15656. |
| [24] | Bingham, T. W.; Hernandez, L. W.; Olson, D. G.; Svec, R. L.; Hergenrother, P. J.; Sarlah, D. J. Am. Chem. Soc. 2019, 141, 657. |
| [25] | Liang, L.; Li, J.; Shen, B.; Zhang, Y.; Liu, J.; Chen, J.; Liu, D. Org. Biomol. Chem. 2021, 19, 2767. |
| [26] | Ding, F.; Liang, L.; Yao, J.; Wang, B.; Xu, C.; Liu, D. Org. Lett. 2022, 24, 9458. |
/
| 〈 |
|
〉 |