Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Iodoenol Lactone Derivatives from the Baylis-Hillman Adducts Using Iodolactonization Protocol

  • Saravanan, GowriSankar (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Mi-Jung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Sang-Ku (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2004.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. GowriSankar, S.; Lee, K. Y.; Lee, C. G.; Kim, J. N. TetrahedronLett. 2004, 45, 6141 and further references cited therein for theBaylis-Hillman reaction. https://doi.org/10.1016/j.tetlet.2004.06.057
  2. Wu, Z.; Minhas, G. S.; Wen, D.; Jiang, H.; Chen, K.;Zimniak, P.; Zheng, J. J. Med. Chem. 2004, 47, 3282. https://doi.org/10.1021/jm0499615
  3. Doi, J.T.; Luehr, G. W.; Carmen, D. D.; Lippsmeyer, B. C. J. Org. Chem.1989, 54, 2764. https://doi.org/10.1021/jo00272a061
  4. Biagetti, M.; Bellina, F.; Carpita, A.; Viel, S.;Mannina, L.; Rossi, R. Eur. J. Org. Chem. 2002, 1063.
  5. Bellina,F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron 2001, 57, 2857 and further references cited therein. https://doi.org/10.1016/S0040-4020(01)00139-9
  6. Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68,5936. https://doi.org/10.1021/jo034308v
  7. Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999,64, 8770. https://doi.org/10.1021/jo9821628
  8. Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K.C. J. Org. Chem. 1995, 60, 3270. https://doi.org/10.1021/jo00116a003
  9. Vara Prasad, J. V. N.; Para,K. S.; Lunney, E. A.; Ortwine, D. F.; Dunbar, J. B.; Fergunson, D.;Tummino, P. J.; Hupe, D.; Tait, B. D.; Domagala, J. M.; Humblet,C.; Bhat, T. N.; Liu, B.; Guerin, D. A. M.; Baldwin, E. T.;Erickson, J. W.; Sawyer, T. K. J. Am. Chem. Soc. 1994, 116, 6989. https://doi.org/10.1021/ja00094a085
  10. Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L.Tetrahedron 2003, 59, 2067. https://doi.org/10.1016/S0040-4020(03)00212-6
  11. Yao, T.; Larock, R. C. TetrahedronLett. 2002, 43, 7401. https://doi.org/10.1016/S0040-4039(02)01731-8
  12. Biagetti, M.; Bellina, F.; Carpita, A.;Stabile, P.; Rossi, R. Tetrahedron 2002, 58, 5023. https://doi.org/10.1016/S0040-4020(02)00469-6
  13. Oliver, M.A.; Gandour, R. D. J. Org. Chem. 1984, 49, 558. https://doi.org/10.1021/jo00177a038
  14. Bellina, F.;Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett. 2001, 42,2859. https://doi.org/10.1016/S0040-4039(01)00290-8
  15. Grigg, R.; Savic, V. Chem. Commun. 2000, 2381.
  16. Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P.Tetrahedron 1998, 54, 135. https://doi.org/10.1016/S0040-4020(97)10265-4
  17. Haas, J.; Piguel, S.; Wirth, T. Org.Lett. 2001, 4, 297. https://doi.org/10.1021/ol0171113
  18. Dai, W.; Katzenellenbogen, J. A. J. Org.Chem. 1991, 56, 6893. https://doi.org/10.1021/jo00024a035
  19. Ranganathan,S.; Muraleedharan, K. M.; Vaish, N. K.; Jayaraman, N.Tetrahedron 2004, 60, 5273. https://doi.org/10.1016/j.tet.2004.04.014
  20. House, H. O.; Carlson, R. G.;Babad, H. J. Org. Chem. 1963, 28, 3359. https://doi.org/10.1021/jo01047a021
  21. Amaral, L. D.; Melo,S. C. J. Org. Chem. 1973, 38, 800. https://doi.org/10.1021/jo00944a037

Cited by

  1. Synthesis of new N-heteroaryl derivatives of 4-pyrones from kojic acid based Baylis–Hillman acetates vol.48, pp.11, 2013, https://doi.org/10.1007/s10593-013-1188-2
  2. an Intramolecular Friedel-Crafts Alkenylation vol.36, pp.7, 2015, https://doi.org/10.1002/bkcs.10337
  3. Palladium-Catalyzed Alkynylation of Morita–Baylis–Hillman Carbonates with (Triisopropylsilyl)acetylene on Water vol.80, pp.12, 2015, https://doi.org/10.1021/acs.joc.5b00728
  4. Synthesis of Iodoenol Lactone Derivatives from the Baylis—Hillman Adducts Using Iodolactonization Protocol. vol.36, pp.22, 2005, https://doi.org/10.1002/chin.200522099
  5. Baylis-Hillman Reaction and Chemical Transformations of Baylis-Hillman Adducts vol.26, pp.10, 2005, https://doi.org/10.5012/bkcs.2005.26.10.1481
  6. Synthesis of Ene-ynamide Derivatives Starting from Baylis-Hillman Adducts: Isomerization with the Aid of π-Cation Interaction vol.26, pp.9, 2004, https://doi.org/10.5012/bkcs.2005.26.9.1443
  7. A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization vol.48, pp.51, 2004, https://doi.org/10.1016/j.tetlet.2007.10.101
  8. Advances in the Baylis-Hillman reaction-assisted synthesis of cyclic frameworks vol.64, pp.20, 2008, https://doi.org/10.1016/j.tet.2008.02.087