Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Silicon-Tethered Intramolecular [5+2] Oxidopyrylium-Based Cycloaddition and Reductive Cleavage of Ether Bridge: Synthetic Studies Toward Arteminolides

  • Sohn, Jeong-Hun (Department of Chemistry, College of Natural Sciences, Chungnam National University)
  • Received : 2013.09.25
  • Accepted : 2013.10.04
  • Published : 2014.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. (a) Lee, S.-H.; Kim, M.-J.; Bok, S. H.; Lee, H.; Kwon, B.-M. J. Org. Chem. 1998, 63, 7111. https://doi.org/10.1021/jo980919p
  2. (b) Lee, S.-H.; Kang, H.-M.; Song, H.-C.; Lee, H.; Lee, U. C.; Son, K.-H.; Kim, S.-H.; Kwon, B.-M. Tetrahedron 2000, 56, 4711. https://doi.org/10.1016/S0040-4020(00)00394-X
  3. (c) Lee, S.-H.; Kim, H.-K.; Seo, J.- M.; Kang, H.-M.; Kim, J.-H.; Son, K.-H.; Lee, H.; Kwon, B.-M.; Shin, J.; Seo, Y. J. Org. Chem. 2002, 67, 7670. https://doi.org/10.1021/jo020299z
  4. (d) Lee, S.-H.; Lee, M.-Y.; Kang, H.-M.; Han, D. C.; Son, K.-H.; Yang, D. C.; Sung, N.-D.; Lee, C. W.; Kim, H. M.; Kwon, B.-M. Bioorg. Med. Chem. 2003, 11, 4545. https://doi.org/10.1016/j.bmc.2003.08.008
  5. (a) Zhang, F. L.; Casey, P. J. Ann. Rev. Biochem. 1996, 65, 241. https://doi.org/10.1146/annurev.bi.65.070196.001325
  6. (b) Agrawal, A. G.; Somani, R. R. Mini-Rev. Med. Chem. 2009, 9, 638. https://doi.org/10.2174/138955709788452702
  7. (a) Lee, H.-Y.; Sohn, J.-H.; Kim, H. Y.; Kwon, B.-M. Tetrahedron Lett. 2001, 42, 1695. https://doi.org/10.1016/S0040-4039(00)02324-8
  8. (b) Sohn, J.-H. Bull. Korean Chem. Soc. 2009, 30, 2517. https://doi.org/10.5012/bkcs.2009.30.11.2517
  9. (c) Sohn, J.-H. Bull. Korean Chem. Soc. 2010, 31, 1841. https://doi.org/10.5012/bkcs.2010.31.7.1841
  10. (d) Sohn, J.- H. Bull. Korean Chem. Soc. 2012, 33, 289. https://doi.org/10.5012/bkcs.2012.33.1.289
  11. (a) Jakupovic, J.; Chem, Z.-L.; Bohlmann, F. Phytochemistry 1987, 26, 2777. https://doi.org/10.1016/S0031-9422(00)83589-X
  12. (b) Bohlman, F; Zdero, C. Phytochemistry 1978, 17, 1595. https://doi.org/10.1016/S0031-9422(00)94650-8
  13. (c) Zhang, W.; Luo, S.; Fang, F.; Chen, Q.; Hu, H.; Jia, X.; Zhai, H. J. Am. Chem. Soc. 2005, 127, 18. https://doi.org/10.1021/ja0439219
  14. (d) Wong, H.-F.; Brown, G. D. J. Nat. Prod. 2002, 65, 481. https://doi.org/10.1021/np0103113
  15. (a) Tamao, K.; Kawachi, A.; Tanaka, Y.; Ohtani, H.; Ito, Y. Tetrahedron 1996, 52, 5765. https://doi.org/10.1016/0040-4020(96)00212-8
  16. (b) Fleming, I. Chem. Rev. 1997, 97, 2063. https://doi.org/10.1021/cr941074u
  17. (a) Singh, V.; Krishna, U. M.; Vikrant; Trivedi, G. K. Tetrahedron 2008, 64, 3405. https://doi.org/10.1016/j.tet.2008.01.049
  18. (b) Pellissier, H. Adv. Synth. Catal. 2011, 353, 189. https://doi.org/10.1002/adsc.201000695
  19. (c) Katritzky, A. R.; Dennis, N. Chem. Rev. 1989, 89, 827. https://doi.org/10.1021/cr00094a006
  20. Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976. https://doi.org/10.1021/ja972279y
  21. Lefebvre, Y. Tetrahedron Lett. 1972, 13, 133. https://doi.org/10.1016/S0040-4039(01)84259-3

Cited by

  1. ) sequences vol.50, pp.65, 2014, https://doi.org/10.1039/C4CC04163A
  2. Recent Developments in the [5+2] Cycloaddition vol.360, pp.8, 2018, https://doi.org/10.1002/adsc.201701379
  3. ChemInform Abstract: Silicon‐Tethered Intramolecular [5 + 2] Oxidopyrylium‐Based Cycloaddition and Reductive Cleavage of Ether Bridge: Synthetic Studies Toward Arteminolides. vol.45, pp.20, 2014, https://doi.org/10.1002/chin.201420187
  4. Further Investigation of Pyranone Activation vol.91, pp.1, 2014, https://doi.org/10.3987/com-14-13131