Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Mild Isomerative Opening of Tetrahydrofuranyl Subunits in Steroids Using TFAT (trifluoroacetyl trifluoromethanesulfonate): Application to Synthesis of C17-OH Rockogenin Acetate

  • Lee, Jong-Seok (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute) ;
  • Kim, Byung-Sook (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute) ;
  • Shin, Jun-Ho (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute) ;
  • Lee, Yeon-Ju (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute) ;
  • Shin, Hee-Jae (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute) ;
  • Lee, Hyi-Seung (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
  • Received : 2011.10.20
  • Accepted : 2011.11.02
  • Published : 2012.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

A novel and efficient tetrahydrofuranyl ring opening method was developed using the highly reactive TFAT reagent in the presence of an acid scavenger, 2,6-di-tert-butyl-4-methylpyridine. Various acid sensitive groups are compatible with the reaction condition, making it generally applicable to many tetrahydrofuranyl steroids. Moreover, it is a synthetic equivalent of 'Marker degradation' affording an efficient synthesis of C17-OH rockogenin acetate.

Keywords

References

  1. Green, T. W.; Wuts, P. G. Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons, Inc.: Hoboken, New Jersy, 2007; Chapter 2.
  2. Forbus, T. R., Jr.; Taylor, S. L.; Martin, J. C. J. Org. Chem. 1987, 52, 4156. https://doi.org/10.1021/jo00228a002
  3. Mandal, A. K.; Soni, N. R.; Ratnam, K. R. Synthesis 1985, 274.
  4. Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761. https://doi.org/10.1021/jo00443a033
  5. Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247. https://doi.org/10.1021/jo01322a012
  6. Crombie, L.; Rainbow, L. J. J. Chem. Soc. Perkin Trans. 1 1994, 673.
  7. Mudry, B.; Cohen, T. J. Am. Chem. Soc. 1991, 113, 1866. https://doi.org/10.1021/ja00005a080
  8. Lee, J. S.; Fuchs, P. L. J. Am. Chem. Soc. 2005, 127, 13122. https://doi.org/10.1021/ja0531935
  9. Fortner, K. C.; Kato, D.; Tanaka, Y.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 275. https://doi.org/10.1021/ja906996c
  10. Fortner, K. C.; Kato, D.; Tanaka, Y.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 275. https://doi.org/10.1021/ja906996c
  11. Shi, Y.; Jia, L.; Xiao, Q.; Lan, Q.; Tang, X.; Wang, D.; Li, M.; Ji, Y.; Zhou, T.; Tian, W. Chem. Asian J. 2011, 6, 786. https://doi.org/10.1002/asia.201000882
  12. Izgu, E. C.; Burns, A. C.; Hoye, T. R. Org. Lett. 2011, 13, 703. https://doi.org/10.1021/ol102936z
  13. Welzel, P.; Janssen, B.; Duddeck, H. Liebigs Ann. Chem. 1981, 546.
  14. Iglesias-Arteaga, M. A.; Arcos-Ramos, R. O. Tetrahedron Lett. 2006, 47, 8029. https://doi.org/10.1016/j.tetlet.2006.09.078
  15. Lee, S.; Jamieson, D.; Fuchs, P. L. Org. Lett. 2009, 11, 5. https://doi.org/10.1021/ol802122p
  16. Jiang, B.; Shi, H.-P.; Xu, M.; Wang, W.-J.; Zhou, W.-S. Tetrahedron 2008, 64, 9738. https://doi.org/10.1016/j.tet.2008.07.091
  17. Izzo, I.; Di Filippo, M.; Napolitano, R.; De Riccardis, F. Eur. J. Org. Chem. 1999, 3505.
  18. Chen, L.-J.; Xu, Q.-H.; Huang, H.; Lin, J.-R.; Tian, W.-S. Tetrahedron Lett. 2007, 48, 3475. https://doi.org/10.1016/j.tetlet.2007.03.001
  19. Lee, J. S.; Fuchs, P. L. Org. Lett. 2003, 5, 3619. https://doi.org/10.1021/ol035284h
  20. Marker, R. E.; Rohrmann, E. J. Am. Chem. Soc. 1939, 61, 846. https://doi.org/10.1021/ja01873a020
  21. Marker, R. E.; Krueger, J. J. Am. Chem. Soc. 1940, 62, 3349. https://doi.org/10.1021/ja01869a023
  22. Marker, R. E. J. Am. Chem. Soc. 1940, 62, 2543. https://doi.org/10.1021/ja01866a077
  23. Woodward, R. B.; Sondheimer, F.; Taub, D. J. Am. Chem. Soc. 1951, 73, 4057.
  24. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157. https://doi.org/10.1021/ja00145a045
  25. Jeong, J. U.; Guo, C.; Fuchs, P. L. J. Am. Chem. Soc. 1999, 121, 2071. https://doi.org/10.1021/ja9817141
  26. LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692. https://doi.org/10.1021/ja972160p
  27. Lee, J. S. Encyclopedia of Reagents for Organic Synthesis, 2nd ed.; Paquette, L. A., Crich, D., Fuchs, P. L., Molander, G. A., Eds.; John Wiley & Sons, Ltd.: Chichester, West Sussex, 2009; Vol. 12, p 9989.
  28. Lee, J. S. Ph.D. Dissertation, Purdue University, West Lafayette, IN, 2005.
  29. Lee, S.; Fuchs, P. L. Org. Lett. 2004, 6, 1437. https://doi.org/10.1021/ol049712a
  30. Velgova, H.; Kasal, A.; Budesinsky, M. Steroids 1994, 59, 335. https://doi.org/10.1016/0039-128X(94)90123-6
  31. Toro, A.; Pallagi, I.; Ambrus, G. Tetrahedron Lett. 1994, 35, 7651. https://doi.org/10.1016/S0040-4039(00)78366-3
  32. Kim, M.; Kawada, K.; Gross, R. S.; Watt, D. S. J. Org. Chem. 1990, 55, 504. https://doi.org/10.1021/jo00289a023
  33. De Munari, S.; Frigerio, M.; Santagostino, M. J. Org. Chem. 1996, 61, 9272. https://doi.org/10.1021/jo961044m
  34. Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1997, 1, 3291.
  35. Lee, J. S. Ph.D. Dissertation, Purdue University, West Lafayette, IN, 2005.
  36. Cekovic, Z. Tetrahedron 2003, 59, 8073. https://doi.org/10.1016/S0040-4020(03)01202-X
  37. Feray, L.; Kuznetsov, N.; Renaud, P. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 246.
  38. Ravindar, K.; Reddy, M. S.; Lindqvist, L.; Pelletier, J.; Deslongchamps, P. J. Org. Chem. 2011, 76, 1269. https://doi.org/10.1021/jo102054r
  39. Lee, J. S.; Fuchs, P. L. Org. Lett. 2003, 5, 2247. https://doi.org/10.1021/ol034551g
  40. Betancor, C.; Freire, R.; Perez-Martin, I.; Prange, T.; Suarez, E. Org. Lett. 2002, 4, 1295. https://doi.org/10.1021/ol025580e
  41. Lee, S.; LaCour, T. G.; Lantrip, D.; Fuchs, P. L. Org. Lett. 2002, 4, 313. https://doi.org/10.1021/ol0165894
  42. Lee, S.; Fuchs, P. L. Org. Lett. 2002, 4, 317. https://doi.org/10.1021/ol016572l
  43. Barrero, A. F.; Oltra, J. E.; Alvarez, M.; Rosales, A. J. Org. Chem. 2002, 67, 5461. https://doi.org/10.1021/jo0256538
  44. Barrero, A. F.; Oltra, J. E.; Alvarez, M. Tetrahedron Lett. 2000, 41, 7639. https://doi.org/10.1016/S0040-4039(00)01334-4
  45. Chatgilialoglu, C.; Gimisis, T.; Spada, G. P. Chem.-Eur. J. 1999, 2866.
  46. Allen, P. A.; Brimble, M. A.; Prabaharan, H. Synlett 1999, 295.
  47. Petrovic, G.; Saicic, R. N.; Cekovic, Z. Synlett 1999, 635.

Cited by

  1. Synthesis of the aglycon of aspafiliosides E and F based on cascade reactions vol.52, pp.9, 2016, https://doi.org/10.1039/C5CC08856A