Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Formal Synthesis of Racemic Herbertene, α-Herbertenol, β-Herbertenol and Herbertenone via Gold(I)-Catalyzed Cyclization of 5-Phenyl-5-siloxy-3-en-1-ynes

  • Received : 2012.10.10
  • Accepted : 2012.10.21
  • Published : 2013.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Asakawa, Y.; Matsuda, R.; Schofield, W. B.; Gradstein, S. R. Phytochemistry 1982, 21, 2471. https://doi.org/10.1016/0031-9422(82)85243-6
  2. Ho, T. L.; Chang, M. H. Tetrahedron Lett. 1994, 35, 4819. https://doi.org/10.1016/S0040-4039(00)76977-2
  3. Erdtman, H.; Thomas, B. R. Acta Chem. Scand. 1958, 12, 267. https://doi.org/10.3891/acta.chem.scand.12-0267
  4. Enzell, C.; Erdtman, H. Tetrahedron 1958, 4, 361. https://doi.org/10.1016/0040-4020(58)80057-5
  5. Matsuo, A.; Yuki, S.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1981, 864.
  6. Matsuo, A.; Yuki, S.; Nakayama, M.; Hayashi, S. Chem. Lett. 1982, 463.
  7. Buchanan, M. S.; Connolly, J. D.; Rycroft, D. S. Phytochemistry 1996, 43, 1245. https://doi.org/10.1016/S0031-9422(96)00512-2
  8. Feld, H.; Zapp, J.; Becker, H. Phytochemistry 2003, 64, 1335. https://doi.org/10.1016/j.phytochem.2003.08.021
  9. Irita, H.; Hashimoto, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 2000, 55, 247. https://doi.org/10.1016/S0031-9422(00)00317-4
  10. Chandrasekaran, S.; Turner, J. V. Tetrahedon Lett. 1982, 23, 3799. https://doi.org/10.1016/S0040-4039(00)87711-4
  11. Saha, A. K.; Das, S.; Mukherjee, D. Tetrahedron Lett. 1994, 35, 3353. https://doi.org/10.1016/S0040-4039(00)76905-X
  12. Mandelt, K.; Fitjer, L. Synthesis 1998, 1523.
  13. Nayek, A.; Ghosh, S. Tetrahedron Lett. 2002, 43, 1313. https://doi.org/10.1016/S0040-4039(01)02365-6
  14. Bernard, A. M.; Frongia, A.; Secci, F.; Piras, P. P. Chem. Commun. 2005, 3853.
  15. Srikrishna, A.; Ravikumar, P. C.; Krishnan, H. S. Synthesis 2008, 10, 1527.
  16. An, S. E.; Jeong, J.; Baskar, B.; Lee, J.; Seo, J.; Rhee, Y. H. Chem. Eur. J. 2009, 15, 11837. https://doi.org/10.1002/chem.200901824
  17. Gibson, S. E.; Lewis, S. E.; Mainolfi, N. J. Orgnomet. Chem. 2004, 689, 3873. https://doi.org/10.1016/j.jorganchem.2004.04.045
  18. Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802. https://doi.org/10.1021/ja051689g
  19. Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442. https://doi.org/10.1021/ja057327q
  20. Jin, T.; Yamamoto, Y. Org. Lett. 2008, 10, 3137. https://doi.org/10.1021/ol801265s
  21. Oh, C. H.; Karmakar, S. J. Org. Chem. 2009, 74, 370. https://doi.org/10.1021/jo802103g
  22. Pal, A.; Gupta, P. D.; Roy, A.; Mukherjee, D. Tetrahedron Lett. 1999, 40, 4733. https://doi.org/10.1016/S0040-4039(99)00835-7
  23. Gupta, P. D.; Pal, A.; Roy, A.; Mukherjee, D. Tetrahedron Lett. 2000, 41, 7563. https://doi.org/10.1016/S0040-4039(00)01298-3
  24. Srikrishna, A.; Rao, M. S. Synlett 2002, 2, 340.
  25. Matsuda, T.; Shigeno, M.; Makino, M.; Murakami, M. Org. Lett. 2006, 8, 3379. https://doi.org/10.1021/ol061359g
  26. Chavan, S. P.; Thakkar, M.; Kharul, R. K.; Pathak, A. B.; Bhosekar, G. V.; Bhadbhade, M. M. Tetrahedron 2005, 61, 3873. https://doi.org/10.1016/j.tet.2005.01.050
  27. Srikrishna, A.; Lakshmi, B. V. Tetrahedron Lett. 2005, 46, 487 https://doi.org/10.1016/j.tetlet.2004.11.113

Cited by

  1. Gold catalysis in total synthesis – recent achievements vol.45, pp.5, 2016, https://doi.org/10.1039/C5CS00721F