DOI QR코드

DOI QR Code

Gold-Catalyzed Cycloisomerization of (2-Alkynyl-1-cycloalkenyl)methanols to Highly Substituted Furans

  • 발행 : 2010.03.20

초록

A new and efficient Au-catalyzed alkoxycyclization of conjugated enynols offers a general entry to a wide range of highly substituted furans in good to excellent yields. These furans were subjected to diethyl acetylenedicarcoxylate to afford the interesting cycloadducts in good to excellent yields.

키워드

참고문헌

  1. Heaney, H.; Ahn, J. S. In ComprehensiveHeterocyclic Chemistr II; Katritzky, A. R., Rees, C. W., Scriven,E. F. V, Eds.; Pergamon Press: Oxford, 1996; Vol. 2, pp 297-436.
  2. Lipshutz, B. H. Chem. Rev. 1986, 86, 795. https://doi.org/10.1021/cr00075a005
  3. Westley, J. W.Polyether Antibiotics: Naturally Occurring Acid Ionophore;Marcel Dekker: New York, 1982.
  4. Piggott, M. J.; Wege, D. Tetrahedron2006, 62, 3550. https://doi.org/10.1016/j.tet.2006.01.096
  5. Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, G. J. Org. Chem.1982, 52, 1680. https://doi.org/10.1021/jo00385a007
  6. Goldsmith, D. J.; Kennedy, E.; Campbell, R. G.J. Org. Chem. 1975, 40, 3571. https://doi.org/10.1021/jo00912a022
  7. Lisphutz, B. H. Chem. Rev. 1986,86, 795. https://doi.org/10.1021/cr00075a005
  8. Brown, R. C. D. Angew. Chem., Int. Ed.2005, 44, 850. https://doi.org/10.1002/anie.200461668
  9. Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progressin Heterocyclic Chemistry; Gribble, G. W., Gilchrist T. L., Eds.;Pergamon Press: Oxford, 2002; Vol. 14, pp 139-179.
  10. Keay,B. A. Chem. Soc. Rev. 1999, 28, 209. https://doi.org/10.1039/a809439j
  11. Fukuda, Y.; Shiragami, H.; Utimoto,K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816. https://doi.org/10.1021/jo00020a024
  12. Arcadi, A.; Cacchi,S.; Larock, R. C.; Marinelli, F. Tetrahedron Lett. 1993, 34,2813. https://doi.org/10.1016/S0040-4039(00)73569-6
  13. Trost, B. M.; Mcintosh, M. C. J. Am. Chem. Soc. 1995,117. 7255. https://doi.org/10.1021/ja00132a030
  14. Cabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem.1999, 64, 7687. https://doi.org/10.1021/jo990847h
  15. Luo, F.-T.; Bajji, A. C.; Jeevanandam, A. J.Org. Chem. 1999, 64, 1738. https://doi.org/10.1021/jo981975t
  16. Ma, S.; Zhang, J. Chem. Commun.2000, 117.
  17. Ma, S.; Zhang, J.; Lu, L. Chem. Eur. J. 2003, 9, 2447. https://doi.org/10.1002/chem.200204664
  18. Aurrecoechea, J. M.; Pere, E. Tetrahedron Lett. 2004, 604, 139
  19. Seiller, B.; Bruneau, C.; Dixneuf, P. H.Tetrahedron 1995, 51, 1308
  20. Marshall,J. A.; Wang, W.-J. J. Org. Chem. 1991, 56, 960. https://doi.org/10.1021/jo00003a013
  21. Marshall, J. A.;Bartley, G. S. J. Org. Chem. 1994, 59, 7169 https://doi.org/10.1021/jo00102a056
  22. Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537 https://doi.org/10.1021/ol016205+
  23. Hashimi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew.Chem., Int. Ed. 2003, 39, 2285.
  24. Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409. https://doi.org/10.1021/ol052160r
  25. Yao, T.; Zhang, X.; Larock,R. C. J. Am. Chem. Soc. 2004, 126, 11164. https://doi.org/10.1021/ja0466964
  26. Yao, T.; Zhang,X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679. https://doi.org/10.1021/jo0510585
  27. Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801. https://doi.org/10.1021/ja9941781
  28. Mendez, M.; Munoz, M. P.; Nevado, C.; Cardenas, D. J.; Echavarren,A. M. J. Am. Chem. Soc. 2001, 123, 10511. https://doi.org/10.1021/ja0112184
  29. Furstner, A.;Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863. https://doi.org/10.1021/ja0109343
  30. Mendez, M.; Echavarren, A. M. Eur. J. Org. Chem. 2002, 15.
  31. Aubert, C.; Busine, O.; Malacria, M. Chem. Rev. 2002, 102,813. https://doi.org/10.1021/cr980054f
  32. McDonald, F. E. Chem. Eur. 1999, 5, 3103. https://doi.org/10.1002/(SICI)1521-3765(19991105)5:11<3103::AID-CHEM3103>3.0.CO;2-N
  33. Nevado, C.; Charruault, L.; Michelet, V.; Nieto-Oberhuber, C.;Munoz, M. P.; Mendez, M.; Rager, M.-N.; Genet, J.-P.; Echavarren,A. M. Eur. J. Org. Chem. 2003, 706.
  34. Nevado, C.; Cardenas,D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627. https://doi.org/10.1002/chem.200204646
  35. Martin-Matute, B.; Nevado, C.; Cardenas, D. K.; Echavarren, A.M. J. Am. Chem. Soc. 2003, 125, 5757. https://doi.org/10.1021/ja029125p
  36. Mendez, M.; Mumoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 122, 11549. https://doi.org/10.1021/ja002577m
  37. Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126,11164. https://doi.org/10.1021/ja0466964
  38. Oh, C. H.; Reddy, V. R.; Kim, A.; Rhim, C. Y. TetrahedronLett. 2006, 47, 5307. https://doi.org/10.1016/j.tetlet.2006.05.119
  39. Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4531. https://doi.org/10.1021/jo050191u
  40. Cadierno, V.; Diez J.; Gimeno, J.; Nebra, N. J. Org. Chem.2008, 73(15), 5852. https://doi.org/10.1021/jo800726u
  41. Pridmore, S. J.; Slatford, P. A.; Williams,M. J. Tetrahedron Lett. 2007, 48, 5111. https://doi.org/10.1016/j.tetlet.2007.05.069
  42. Gabriele, B.; Plastina, P.; Salerno, G.; Mancuso, R. Synthesis2006, 4247.
  43. Liu, Y.; Song, F.; Cong, L. J. Org. Chem. 2005, 70,6999. https://doi.org/10.1021/jo050966z
  44. Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7,5409. https://doi.org/10.1021/ol052160r

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  4. Recent advances in terpenoid syntheses from China vol.59, pp.9, 2016, https://doi.org/10.1007/s11426-016-0076-6
  5. Total synthesis of sesterterpenoids pp.1460-4752, 2019, https://doi.org/10.1039/C8NP00050F
  6. thermodynamic control vol.54, pp.23, 2018, https://doi.org/10.1039/C7CC09466C
  7. Iridium(I)‐Catalyzed Coupling of (Z)‐2‐En‐4‐yn‐1‐ols with Activated Alkynes: A New Synthetic Route to 7‐Oxanorbornadienes vol.352, pp.14, 2010, https://doi.org/10.1002/adsc.201000408
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  9. Palladium-catalyzed cycloisomerization of (Z)-enynols into furans using green solvents: glycerol vs. water vol.12, pp.9, 2010, https://doi.org/10.1039/c0gc00169d
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  16. Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes vol.121, pp.14, 2010, https://doi.org/10.1021/acs.chemrev.0c00788
  17. Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes vol.57, pp.9, 2021, https://doi.org/10.1007/s10593-021-03005-2