Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

First Total Synthesis of Isopsoralenoside

Author(s): Min Wu, Lijia Xu, Mingwei Song, Ying Li, Yingying Wang and Hongbo Dong*

Volume 19, Issue 10, 2022

Published on: 16 February, 2022

Page: [832 - 836] Pages: 5

DOI: 10.2174/1570178619666220111115718

Price: $65

Abstract

The first total synthesis of the natural product iopsoralenoside, isolated from the n-butyl alcohol extract of Fructus Psoraleae (FP), was achieved in 17% yield over 7 steps. The key steps of the process were glycosylation and irradiation promoted by ultraviolet light. This synthesis provided a sufficient amount of synthesized trans- and cis-isopsoralenoside for further bioassays.

Keywords: Total synthesis, natural products, isopsoralenoside, fructus psoraleae, compounds, fabaceae.

« Previous Next »
Graphical Abstract

[1]
National Commission of Chinese Pharmacopoeia. Pharmacopoeia of the People’s Republic of China; Chinese Medical Science and Technology Press: Beijing, 2015, 1, pp. 188-119.
[2]
Chen, Z.; Li, C.; Qian, Y.H.; Fu, Y.; Feng, Z.M. J. Asian Nat. Prod. Res., 2020, 22(2), 179-192.
[http://dx.doi.org/10.1080/10286020.2018.1537265] [PMID: 30621446]
[3]
Wang, J.; Wang, G.; Gong, L.; Sun, G.; Shi, B.; Bao, H.; Duan, Y. Mol. Med. Rep., 2018, 17(1), 1125-1131.
[PMID: 29115612]
[4]
Li, X.M.; Yang, Q.; Li, X.B.; Cheng, Q.; Zhang, K.; Han, J.; Zhao, J.N.; Liu, G.; Zhao, M.G. Metab. Brain Dis., 2017, 32(1), 259-265.
[http://dx.doi.org/10.1007/s11011-016-9913-z] [PMID: 27670769]
[5]
Qiao, C.F.; Han, Q.B.; Mo, S.F.; Song, J.Z.; Xu, L.J.; Chen, S.L.; Yang, D.J.; Kong, L.D.; Kung, H.F.; Xu, H.X. Chem. Pharm. Bull. (Tokyo), 2006, 54(5), 714-716.
[http://dx.doi.org/10.1248/cpb.54.714] [PMID: 16651775]
[6]
Hamed, A.; Springuel, I.; El-Emary, N. Phytochemistry, 1999, 50(5), 887-890.
[http://dx.doi.org/10.1016/S0031-9422(98)00521-4]
[7]
Ren, J.; Wang, W. B.; Zhang, M. J.; Hu, K.; Li, l. X.; Yuan, L. China Patent C, 2019. ,(110128382A), 16.
[8]
Yong, R.L. Tetrahedron Lett., 1995, 51(11), 3087-3094.
[http://dx.doi.org/10.1016/0040-4020(95)00070-O]
[9]
Huang, H.; Li, F.; Xu, Z.; Cai, J.; Ji, X.; Deng, G-J. Adv. Synth. Catal., 2017, 359(18), 3102-3107.
[http://dx.doi.org/10.1002/adsc.201700730]
[10]
Dong, H.B.; Hou, M.; Ma, W.B.; Zhang, J.X.; Li, Z.Y.; Luo, H.B.; Tang, K.H.; Cao, S.H. J. Asian Nat. Prod. Res., 2018, 20(12), 1154-1161.
[http://dx.doi.org/10.1080/10286020.2017.1379511] [PMID: 28948834]
[11]
Horaguchi, T.; Hosokawa, N.; Tanemura, K.; Suzuki, T. J. Heterocycl. Chem., 2002, 39(1), 61-67.
[http://dx.doi.org/10.1002/jhet.5570390108]
[12]
You, C.; Zhang, Z.; Tu, Y.; Tang, H.; Wang, Y.; Long, D.; Zhao, J. J. Org. Chem., 2020, 85(5), 3902-3910.
[http://dx.doi.org/10.1021/acs.joc.9b03006] [PMID: 31944121]
[13]
Zou, Y.; Lobera, M.; Snider, B.B. J. Org. Chem., 2005, 70(5), 1761-1770.
[http://dx.doi.org/10.1021/jo047974k] [PMID: 15730299]

Rights & Permissions Print Cite
Article Metrics
17
1
© 2024 Bentham Science Publishers | Privacy Policy