DOI QR코드

DOI QR Code

Stereoselective Cylization of Allenoates Containing Carbonyl Functionalities Mediated Mo(CO)6: Synthesis of Canadensolide and Sporothriolide

  • Kwon, Ji-Sook (Department of Chemistry, Sungkyunkwan University) ;
  • Gong, Su-Yeon (Department of Chemistry, Sungkyunkwan University) ;
  • Woo, Seok-Hoon (Department of Chemistry, Sungkyunkwan University) ;
  • Yu, Chan-Mo (Department of Chemistry, Sungkyunkwan University)
  • 발행 : 2009.04.20

초록

키워드

참고문헌

  1. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. https://doi.org/10.1021/cr0683966
  2. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644. https://doi.org/10.1021/cr980054f
  3. Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067. https://doi.org/10.1021/ar010068z
  4. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. https://doi.org/10.1021/cr980054f
  5. Trost, B. M. Acc. Chem. Res. 2002, 35, 695. https://doi.org/10.1002/anie.200503863
  6. Ma, S. Eur. J. Org. Chem. 2004, 1175. https://doi.org/10.1021/ol7026569
  7. Mandai, T. In Modern Allene Chemistry, Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 925-972. https://doi.org/10.1039/jr9630005385
  8. Yu, C.-M.; Youn, J.; Jung, J. Angew. Chem. Int. Ed. 2006, 45, 1553. https://doi.org/10.1016/j.tet.2008.01.009
  9. Yu, C.-M.; Hong, Y.-T.; Lee, J. J. Org. Chem. 2004, 69, 8506. https://doi.org/10.1021/ja0684186
  10. Yu, C.-M.; Hong, Y.-T.; Yoon, S.-K.; Lee, J. Synlett 2004, 1695.
  11. Yu, C.-M.; Youn, J.; Lee, M.-K. Org. Lett. 2005, 7, 3733. https://doi.org/10.1021/ol0513701
  12. Yu, C.-M.; Youn, J.; Jung, H.-K. Bull. Korean Chem. Soc. 2006, 27, 463. https://doi.org/10.5012/bkcs.2006.27.4.463
  13. Ko, K.-J.; Kim, S. H.; Kim, Y.; Min, D.; Yu, C.-M. Bull. Korean Chem. Soc. 2007, 28, 1921. https://doi.org/10.5012/bkcs.2007.28.11.1921
  14. Kim, S. H.; Oh, S.-J.; Ho, P.-S.; Kang, S.-C.; O, K.-J.; Yu, C.-M. Org. Lett. 2008, 10, 265. https://doi.org/10.1021/ol7026569
  15. Brookes, D.; Tidd, B. K.; Turner, W. B. J. Chem. Soc. 1963, 5385. https://doi.org/10.1039/jr9630005385
  16. McCorkindale, N. J.; Wright, J. L. C.; Brain, P. W.; Clarke, S. M.; Hutchinson, S. A. Tetrahedron Lett. 1968, 9, 727. https://doi.org/10.1016/S0040-4039(00)75621-8
  17. Krohn, K.; Ludewig, K.; Aust, H. J.; Draeger, S.; Schulz, B. J. Antibiot. 1994, 47, 113. https://doi.org/10.7164/antibiotics.47.113
  18. Mondal, S.; Ghosh, S. Tetrahedron 2008, 64, 2359. https://doi.org/10.1016/j.tet.2008.01.009
  19. Hon, Y. S.; Hsieh, C. H. Tetrahedron 2006, 62, 9713. https://doi.org/10.1016/j.tet.2006.07.066
  20. Aggarwal, V. K. Davies, P. W. Schmidt, A. T. Chem. Commun. 2004, 1232.
  21. Martin, V. S. Rodriguez, C. M. Martin, T. Org. Prep. Proc. Int. 1998, 30, 291 https://doi.org/10.1080/00304949809355291
  22. Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 778. https://doi.org/10.1021/ja0684186
  23. Brummond, K. M.; Curran, D. P.; Mitasev, B.; Fischer, S. J. Org. Chem. 2005, 70, 1745. https://doi.org/10.1021/jo0481607
  24. Cao, H.; Van Ornui, S. G.; Deschamps, J.; Flippen-Anderson, J.; Laib, F.; Cook, J. M. J. Am. Chem. Soc. 2005, 127, 933. https://doi.org/10.1021/ja040120x

피인용 문헌

  1. Three Carbons for Complexity! Recent Developments of Palladium-Catalyzed Reactions of Allenes vol.5, pp.8, 2013, https://doi.org/10.1002/cctc.201200875
  2. Total Synthesis of (−)-Dihydrosporothriolide Utilizing an Indium-Mediated Reformatsky–Claisen Rearrangement vol.79, pp.12, 2014, https://doi.org/10.1021/jo5008948
  3. : Synthesis of Canadensolide and Sporothriolide. vol.40, pp.36, 2009, https://doi.org/10.1002/chin.200936207
  4. Intramolecular Carbocyclization of Allenoate-aldehydes with Hexamethylditin Catalyzed by Palladium Complex: Synthesis of Cyclic Dienes vol.31, pp.3, 2009, https://doi.org/10.5012/bkcs.2010.31.03.559
  5. An Intramolecular Cyclocarbonylation of Allenyl Sulfinimides by Molybdenum Carbonyl for the Synthesis of Bicyclic 3-Methylene-1-pyrrol-2-ones vol.32, pp.8, 2009, https://doi.org/10.5012/bkcs.2011.32.8.2873
  6. Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update vol.9, pp.11, 2009, https://doi.org/10.1002/ajoc.202000401
  7. Seven-Step Total Synthesis of Sporothriolide vol.86, pp.17, 2009, https://doi.org/10.1021/acs.joc.1c01663