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. 2011 Dec 23;1(3):129–133. doi: 10.1007/s13659-011-0045-1

Oxidative dearomatic approach towards the synthesis of erythrina skeleton: a formal synthesis of demethoxyerythratidinone

Zhi-Qiang Pan 1, Ji-Xuan Liang 1, Jing-Bo Chen 1, Xiao-Dong Yang 1,✉, Hong-Bin Zhang 1,✉
PMCID: PMC4131647

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. graphic file with name 13659_2011_45_Article_Fig1_HTML.jpg

Keywords: erythrina alkaloid, oxidative dearomation, demethoxyerythratidinone, formal synthesis

Footnotes

This article is published with open access at Springerlink.com

Contributor Information

Xiao-Dong Yang, Email: xdyang@ynu.edu.cn.

Hong-Bin Zhang, Email: zhanghb@ynu.edu.cn.

References

  • [1] (a).Dyke S. F., Quessy S. N. In: The Alkaloids. Rodrigo R. G. A., editor. Academic Press: New York; 1981. pp. 1–98. [Google Scholar]
  • [1] (b).Sano T., Tsuda Y. In: The Alkaloids. Cordell G. A., editor. New York: Academic Press; 1996. pp. 249–337. [Google Scholar]
  • [2].Tanaka H., Tanaka T., Etoh H., Goto S., Terada Y. Heterocycles. 1999;51:2759–2764. doi: 10.3987/COM-99-8686. [DOI] [Google Scholar]
  • [3].Reimann E. Synthesis pathways to erythrina alkaloids and erythrina type compounds. In: Herz W., Falk H., Kirby G. W., editors. Progress in the chemistry of organic natural products. Springer-Verlag/Wien: Austria; 2007. pp. 1–62. [DOI] [PubMed] [Google Scholar]
  • [4].Leete E., Ahmad A. J. Am. Chem. Soc. 1966;88:4722–4725. doi: 10.1021/ja00972a036. [DOI] [PubMed] [Google Scholar]
  • [5] (a).Quideau, S.; Pouysegu, L.; Deffieux, D. Synlett2008, 467–495.
  • [5] (b).Ciufolini, M. A.; Braun, N. A.; Canesi, S.; Ousmer, M.; Chang, J.; Chai, D. Synthesis2007, 3759–3772.
  • [5] (c).Magdziak D., Meek S. J., Pettus T. R. R. Chem. Rev. 2004;104:1383–1430. doi: 10.1021/cr0306900. [DOI] [PubMed] [Google Scholar]
  • [5] (d).Rodrígues, S.; Wipf, P. Synthesis2004, 2767–2783.
  • [5] (e).Van De Water R. W., Pettus T. R. R. Tetrahedron. 2002;58:5367–5405. doi: 10.1016/S0040-4020(02)00496-9. [DOI] [Google Scholar]
  • [6] (a).Xu, Z. X.; Huang, K.; Liu, T.; Xie, M. J.; Zhang, H. B. Chem. Commun. 2011, 4923–4925. [DOI] [PubMed]
  • [6] (b).Liang, J. X.; Chen, J. B.; Liu, J. P.; Li, L.; Zhang, H. B. Chem. Commun. 2010, 3666–3668. [DOI] [PubMed]
  • [6] (c).Liang J. X., Chen J. B., Du F. X., Zeng X. H., Li L., Zhang H. B. Org. Lett. 2009;11:2820–2823. doi: 10.1021/ol901005x. [DOI] [PubMed] [Google Scholar]
  • [7].Gilmore C. D., Allan K. M., Stoltz B. M. J. Am. Chem. Soc. 2008;130:1558–1559. doi: 10.1021/ja0780582. [DOI] [PubMed] [Google Scholar]
  • [8] (a).Zhdankin V. V., Stang P. J. Chem. Rev. 2008;108:5299–5358. doi: 10.1021/cr800332c. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [8] (b).Richardson R. D., Wirth T. Angew. Chem, Int. Ed. 2006;45:4402–4404. doi: 10.1002/anie.200601817. [DOI] [PubMed] [Google Scholar]
  • [8] (c).Wirth T. Angew. Chem. Int. Ed. 2005;44:3656. doi: 10.1002/anie.200500115. [DOI] [PubMed] [Google Scholar]
  • [8] (d).Moriarty R. M. J. Org. Chem. 2005;70:2893–2903. doi: 10.1021/jo050117b. [DOI] [PubMed] [Google Scholar]
  • [8] (e).Zhdankin V. V., Stang P. J. Chem. Rev. 2002;102:2523–2584. doi: 10.1021/cr010003+. [DOI] [PubMed] [Google Scholar]
  • [9] (a).Kita Y., Takada T., Gyoten M., Tohma H., Zenk M. H., Eichhorn J. J. Org. Chem. 1996;61:5857–5864. doi: 10.1021/jo9606766. [DOI] [Google Scholar]
  • [9] (b).Kodama S., Hamashima Y., Nishida K., Node M. Angew. Chem. Int. Ed. 2004;43:2659–2661. doi: 10.1002/anie.200353636. [DOI] [PubMed] [Google Scholar]
  • [10] (a).Sha C. K., Young J. J., Yeh C. P., Chang S. C., Wang S. L. J. Org. Chem. 1991;56:2694–2696. doi: 10.1021/jo00008a023. [DOI] [Google Scholar]
  • [10] (b).Li W. D. Z., Wang X. W. Org. Lett. 2007;9:1211–1214. doi: 10.1021/ol070024b. [DOI] [PubMed] [Google Scholar]
  • [11] (a).Tsuda Y., Nakai A., Ito K., Suzuki F., Haruna M. Heterocycles. 1984;22:1817–1820. doi: 10.3987/R-1984-08-1817. [DOI] [Google Scholar]
  • [11] (b).Joo J. M., David R. A., Yuan Y., Lee C. Org. Lett. 2010;12:5704–5707. doi: 10.1021/ol102535u. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [11] (c).Zhang F., Simpkins N. S., Wilson C. Tetrahedron Lett. 2007;48:5942–5947. doi: 10.1016/j.tetlet.2007.06.111. [DOI] [Google Scholar]
  • [11] (d).Pearson W. H., Kropf J. E., Choy A. L., Lee I. Y., Kampf J. W. J. Org. Chem. 2007;72:4135–4148. doi: 10.1021/jo0703799. [DOI] [PubMed] [Google Scholar]
  • [11] (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. doi: 10.1021/ol0607185. [DOI] [PubMed] [Google Scholar]
  • [11] (f).Wang Q., Padwa A. Org. Lett. 2006;8:601–604. doi: 10.1021/ol0527330. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [11] (g).Padwa A., Wang Q. J. Org. Chem. 2006;71:7391–7402. doi: 10.1021/jo061269p. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [11] (h).Kim G., KimandK J. H., Lee Y. J. Org. Chem. 2006;71:2185–2187. doi: 10.1021/jo052500m. [DOI] [PubMed] [Google Scholar]
  • [11] (i).Stanislawski P. C., Willis A. C., Banwell M. G. Org. Lett. 2006;8:2143–2146. doi: 10.1021/ol060642c. [DOI] [PubMed] [Google Scholar]
  • [11] (j).Allin S. M., Streetley G. B., Slater M., James S. L., Martin W. P. Tetrahedron Lett. 2004;45:5493–5496. doi: 10.1016/j.tetlet.2004.05.060. [DOI] [Google Scholar]
  • [11] (k).Padwa A., Lee H. I., Rashatasakhon P., Rose M. J. Org. Chem. 2004;69:8209–8218. doi: 10.1021/jo048647f. [DOI] [PubMed] [Google Scholar]
  • [11] (l).El Bialy S. A. A., Braun H., Tietze L. F. Angew. Chem. Int. Ed. 2004;43:5391–5393. doi: 10.1002/anie.200460283. [DOI] [PubMed] [Google Scholar]
  • [11] (m).Yasui, Y.; Suzuki, K.; Matsumoto, T. Synlett2004, 619–622.

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