Chinese Journal of Organic Chemistry >
Total Syntheses of Cochlearol F and Didehydroconicol by Biphenyl Boronic Acid
Received date: 2024-04-30
Revised date: 2024-06-20
Online published: 2024-07-18
Total syntheses of Cochlearol F and Didehydroconicol were accomplished through the Suzuki coupling reaction, with the innovative use of biphenylboronic acid. In the total synthesis of Cochlearol F, the key reaction involved the coupling of biphenylboronic acid with enol trifluoromethanesulfonate to construct a new carbon-carbon bond, requiring four steps in total, with an overall yield of 25%. In the total synthesis of Didehydroconicol, the key reaction was the insertion of carbon monoxide into biphenylboronic acid to form a biphenyl lactone, requiring seven steps in total, with an overall yield of 23%. This synthetic strategy will provide a reference for the synthesis of natural products containing biphenyl unit.
Key words: total synthesis; Suzuki cross-coupling; Cochlearol F; Didehydroconicolord
Kai Wang , Jiajun Sui , Chunhong Long , Songjuan Luo , Yongming Chuan , Hongbo Qin . Total Syntheses of Cochlearol F and Didehydroconicol by Biphenyl Boronic Acid[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 343 -348 . DOI: 10.6023/cjoc202404042
| [1] | Peng, X.; Wang, X.; Chen, L.; Yang, H.; Li, L.; Lu, S.; Zhou, L.; Qiu, M. Fitoterapia 2018, 127, 286. |
| [2] | Qin, F.-Y.; Wang, D.-W.; Xu, T.; Zhang, B.-S.; Cheng, Y.-X. Phytochemistry 2022, 199, 113184. |
| [3] | Simon-Levert, A; Arrault, A; Bontemps-Subielos, N.; Canal, C.; Banaigs, B. J. Nat. Prod. 2005, 68, 1412. |
| [4] | Wang, Z.; Tang, Y.; Li, R.; Tian, S.; Tang, Y.; Li, D. Chin. Chem. Lett. 2023, 109247. |
| [5] | Minuti, L.; Ballerini, E.; Barattucci, A.; Bonaccorsi, P. M.; Di Gioia, M. L.; Leggio, A.; Siciliano, C.; Temperini, A. Tetrahedron 2015, 71, 3253. |
| [6] | Zhou, Q. J.; Worm, K.; Dolle, R. E. J. Org. Chem. 2004, 69, 5147. |
| [7] | Hong, L. P.; White, J. M.; Donner, C. D. Aust. J. Chem. 2011, 65, 58. |
| [8] | Shekhar, C.; Satyanarayana, G. Eur. J. Org. Chem 2022, 18, e202101444. |
| [9] | Xia, S.; Gan, L.; Wang, K.; Li, Z.; Ma, D. J. Am. Chem. Soc. 2016, 138, 13493. |
| [10] | Long, Y.; Ding, Y.; Wu, H.; Qu, C.; Liang, H.; Zhang, M.; Zhao, X.; Long, X.; Wang, S.; Puno, P.-T.; Deng, J. Angew. Chem., Int. Ed. 2019, 58, 17552. |
/
| 〈 |
|
〉 |