Natural Products and Bioprospecting    2011, Vol. 1 Issue (3) : 129-133     DOI: 10.1007/s13659-011-0045-1
Regular Article |
Oxidative dearomatic approach towards the synthesis of erythrina skeleton: a formal synthesis of demethoxyerythratidinone
Zhi-Qiang PAN, Ji-Xuan LIANG, Jing-Bo CHEN, Xiao-Dong YANG, Hong-Bin ZHANG
Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, Yunnan, China
Download: PDF(704 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  A concise synthetic route leading to highly functional erythrina alkaloid skeletons has been developed. The key process is an oxidative carbon-carbon coupling followed by a conjugated addition. Based on this new strategy, a formal synthesis of demethoxyerythratidinone was completed in only 6 steps from 4-aminophenol.
Keywords erythrina alkaloid      oxidative dearomation      demethoxyerythratidinone      formal synthesis     
Fund:This work was supported by grants(20925205, 21062026, 2010GA014 and 2009CB522300) from National Natural Science Foundation of China, Yunnan Province and National Basic Research Program of China(973 Program).
Issue Date: 11 February 2018
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Zhi-Qiang PAN
Ji-Xuan LIANG
Jing-Bo CHEN
Xiao-Dong YANG
Hong-Bin ZHANG
Trendmd:   
Cite this article:   
Zhi-Qiang PAN,Ji-Xuan LIANG,Jing-Bo CHEN, et al. Oxidative dearomatic approach towards the synthesis of erythrina skeleton: a formal synthesis of demethoxyerythratidinone[J]. Natural Products and Bioprospecting, 2011, 1(3): 129-133.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-011-0045-1     OR     http://npb.kib.ac.cn/EN/Y2011/V1/I3/129
[1] (a) Dyke, S. F.; Quessy, S. N. The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press:New York, 1981; Vol. 18, pp 1-98. (b) Sano, T.; Tsuda, Y. The Alkaloids; Cordell, G. A., Ed; Academic Press:New York, 1996; Vol. 48, pp 249-337.
[2] Tanaka, H.; Tanaka, T.; Etoh, H.; Goto, S.; Terada, Y. Heterocycles 1999, 51, 2759-2764.
[3] Reimann, E. Synthesis pathways to erythrina alkaloids and erythrina type compounds. in Progress in the chemistry of organic natural products; Herz, W., Falk, H., Kirby, G. W., Ed.; SpringerVerlag/Wien:Austria, 2007; Vol. 88, pp 1-62.
[4] Leete, E.; Ahmad, A. J. Am. Chem. Soc. 1966, 88, 4722-4725.
[5] (a) Quideau, S.; Pouysegu, L.; Deffieux, D. Synlett 2008, 467-495. (b) Ciufolini, M. A.; Braun, N. A.; Canesi, S.; Ousmer, M.; Chang, J.; Chai, D. Synthesis 2007, 3759-3772. (c) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383-1430. (d) Rodrígues, S.; Wipf, P. Synthesis 2004, 2767-2783. (e) Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405.
[6] (a) Xu, Z. X.; Huang, K.; Liu, T.; Xie, M. J.; Zhang, H. B. Chem. Commun. 2011, 4923-4925. (b) Liang, J. X.; Chen, J. B.; Liu, J. P.; Li, L.; Zhang, H. B. Chem. Commun. 2010, 3666-3668. (c) Liang, J. X.; Chen, J. B.; Du, F. X.; Zeng, X. H.; Li, L.; Zhang, H. B. Org. Lett. 2009, 11, 2820-2823.
[7] Gilmore, C. D.; Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 1558-1559.
[8] (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299-5358. (b) Richardson, R. D.; Wirth, T. Angew. Chem, Int. Ed. 2006, 45, 4402-4404. (c) Wirth, T. Angew. Chem. Int. Ed. 2005, 44, 3656. (d) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893-2903. (e) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
[9] (a) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857-5864; (b) Kodama, S.; Hamashima, Y.; Nishida, K.; Node, M. Angew. Chem. Int. Ed. 2004, 43, 2659-2661.
[10] (a) Sha, C. K.; Young, J. J.; Yeh, C. P.; Chang, S. C.; Wang, S. L. J. Org. Chem. 1991, 56, 2694-2696. (b) Li, W. D. Z.; Wang, X. W. Org. Lett. 2007, 9, 1211-1214.
[11] (a) Tsuda, Y.; Nakai, A.; Ito, K.; Suzuki, F.; Haruna, M. Heterocycles 1984, 22, 1817-1820. (b) Joo, J. M.; David, R. A.; Yuan, Y.; Lee, C. Org. Lett. 2010, 12, 5704-5707. (c) Zhang, F.; Simpkins, N. S.; Wilson, C. Tetrahedron Lett. 2007, 48, 5942-5947. (d) Pearson, W. H.; Kropf, J. E.; Choy, A. L.; Lee, I. Y.; Kampf, J. W. J. Org. Chem. 2007, 72, 4135-4148. (e) Gao, S.; Tu, Y. Q.; Hu, X.; Wang, S.; Hua, R.; Jiang, Y.; Zhao, Y.; Fan, X.; Zhang, S. Org. Lett. 2006, 8, 2373-2376. (f) Wang, Q.; Padwa, A. Org. Lett. 2006, 8, 601-604. (g) Padwa, A.; Wang, Q. J. Org. Chem. 2006, 71, 7391-7402. (h) Kim, G.; KimandK, J. H.; Lee, Y. J. Org. Chem. 2006, 71, 2185-2187. (i) Stanislawski, P. C.; Willis, A. C.; Banwell, M. G. Org. Lett. 2006, 8, 2143-2146. (j) Allin, S. M.; Streetley, G. B.; Slater, M.; James, S. L.; Martin, W. P. Tetrahedron Lett. 2004, 45, 5493-5496. (k) Padwa, A.; Lee, H. I.; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2004, 69, 8209-8218. (l) El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Angew. Chem. Int. Ed. 2004, 43, 5391-5393. (m) Yasui, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, 619-622.
No related articles found!
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed