Chinese Journal of Organic Chemistry >
Total Synthesis of Pulchrol and Pulchral
Received date: 2019-07-17
Revised date: 2019-08-20
Online published: 2019-09-05
Supported by
Project supported by the National Natural Science Foundation of China(31800678);the Science and Technology Research Project in ShanXi Province(201801D221062);the Science and Technology Research Project in ShanXi Province(201801D221063);the Shanxi Excellent Doctor Grant Award(SXYBKY201737);the Shanxi Excellent Doctor Grant Award(SXYBKY201706);the Science and Technology Innovation Project of Shanxi Agricultural University(Nos. 2017YJ38);the Science and Technology Innovation Project of Shanxi Agricultural University(2017YJ41)
The total synthesis of natural products pulchrol and pulchral with antiprotozoan activity was reported, starting from the cheap hydroquinone and 4-methylbenzoic acid and using palladium-catalyzed intramolecular decarboxylation coupling reaction of arene carboxylic acids with aryl bromides as the key reaction. This method provides an opportunity for further study of the structure-activity relationship.
Key words: natural product; total synthesis; cross-coupling; pulchrol; pulchral
Dongdong Guo, , Wuxia Zhang, , Weimei Gao, , Xiaodi Guo, , Yongqiang Wang, . Total Synthesis of Pulchrol and Pulchral[J]. Chinese Journal of Organic Chemistry, 2019 , 39(10) : 2936 -2940 . DOI: 10.6023/cjoc201907024
[1] | Marriott, K. S.; Huffman, J. W. Curr. Top. Med. Chem. 2008, 8, 187. |
[2] | Pratap, R.; Ram, V. J. Chem. Rev. 2014, 114, 10476. |
[3] | Wang, X.; Xu, X.; Quan, Z.; Zhang, Z. Chin. J. Org. Chem. 2009, 29, 1821 (in Chinese). |
[3] | ( 王喜存, 许新兵, 权正军, 张彰, 有机化学, 2009, 29, 1821.) |
[4] | (a) Bhattacharya, P.; Senapati, K.; Chattopadhyay, K.; Mandal, S. M.; Basak, A. .RSC Adv 2015, 5, 61562. |
[4] | (b) Mechoulam, R.; McCallum, N. K.; Burstein, S. .Chem. Rev 1976, 76, 75. |
[4] | (c) Sun, W.; Cama, L. D.; Birzin, E. T.; Warrier, S.; Locco, L.; Mosley, R.; Hammond, M. L.; Rohrer, S. P . Bioorg. Med. Chem. Lett. 2006, 16 1468. |
[4] | (d) Radwan, M. M.; Elsohly, M. A.; Slade, D.; Ahmed, S. A.; Khan, I. A.; Ross, S. A . J. Nat. Prod. 2009, 72 906. |
[4] | (e) Simon-Levert, A.; Arrault, A.; Bontemps-Subielos, N.; Canal, C.; Banaigs, B . J. Nat. Prod. 2005, 68 1412. |
[5] | Erosa-Rejón, G. J.; Yam-Puc, A.; Chan-Bacab, M. J.; Giménez-Turbax, A.; Salamanca, E.; Pe?a-Rodríguez, L. M.; Sterner, O. .Phytochem. Lett 2010, 3, 9. |
[6] | Killander, D.; Sterner, O . Eur. J. Org. Chem. 2014,1594. |
[7] | Shen, Z.; Ni, Z.; Mo, S. Wang, J.; Zhu, Y. .Chem.-Eur. J 2012, 18, 4859. |
[8] | Shisodia, S. U.; Punta, C.; Melone, L.; Shisodia, S. U. Curr. Org. Chem. 2013, 17, 1108. |
[9] | Villani, F. J.; Lang, J. J. Am. Chem. Soc. 1950, 72, 2301. |
[10] | Fleifel, A. M. J. Org. Chem. 1960, 25, 1024. |
[11] | Curran, D.; Yang, F.; Cheong, J. J. Am. Chem. Soc. 2002, 124, 14993. |
[12] | Mou, C.; Zhu, T.; Zheng, P.; Yang, S.; Song, B.-A.; Chi, Y. R. Adv. Synth. Catal. 2016, 358, 707. |
[13] | Fan, F.; Dong, J.; Wang, J.; Song, L.; Song, C.; Chang, J. Adv. Synth. Catal. 2014, 356, 1337. |
/
〈 |
|
〉 |