A TBAF-mediated chemoselective method for synthesis of 4-methylbutenolides and 4-hydroxy-4-methylbutenolides from 3-hydroxy-4-(tert-butyldimethylsilyloxy) pentanoates

Chemistry Letters

Volumn 36, Issue 8, 2007, Pages 1058-1059

  Chunhong, Li ^a   Jijun, Xue ^a   Baiyan, Xu ^a   Zhixiang, Xie ^a   Ying, Li ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548308779     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1058     Document Type: Article

References (36)

1. a) Z. Jiang, Y. Chen, R.-Y. Chen, D.-Q. Yu, Phytochemistry 1997, 46, 327.
2. b) Z. Jiang, D.-Q. Yu, J. Nat. Prod. 1997, 60, 122.
3. c) Z. Jiang, Y. Chen, R. Y. Chen, D. Q. Yu, Phytochemistry 1998, 49, 769.
4. d) Y. Chen, R. Y. Chen, Z. Jiang, D. Q. Yu, D. Q. Yu, Planta Med. 1998, 64, 242.
5. e) Z. Jiang, R.-Y. Chen, Y. Chen, D.-Q. Yu, Planta Med. 1998, 64, 362.
6. f) B. S. Mootoo, A. Ali, A. Khan, W. F. Reynolds, S. McLean, J. Nat. Prod. 2000, 63, 807.
7. a) G.-X. Zhao, L. R. Miesbauer, D. L. Smith, J. L. McLaughlin, J. Med. Chem. 1994, 37, 1971.
8. b) D. Cortes, B. Figadere, A. Cavé, Phytochemistry 1993, 32, 1467.
9. a) T. R. Hoye, P. R. Hanson, A. C. Kovelesky, T. D. Ocain, Z. Zhang, J. Am. Chem. Soc. 1991, 113, 9369.
10. b) J. D. White, T. C. Somers, G. N. Reddy, J. Org. Chem. 1992, 57, 4991.
11. c) Z.-J. Yao, Y.-L. Wu, Tetrahedron Lett. 1994, 35, 157.
12. d) T. R. Hoye, P. E. Humpal, J. I. Jiménez, M. J. Mayer, L. Tan, Z. Ye, Tetrahedron Lett. 1994, 35, 7517.
13. e) U. Koert, Tetrahedron Lett. 1994, 35, 2517.
14. f) B. M. Trost, Z. Shi, J. Am. Chem. Soc. 1994, 116, 7459.
15. g) Z.-J. Yao, Y.-L. Wu, J. Org. Chem. 1995, 60, 1170.
16. h) J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989.
17. i) T.-T. He, H.-N. Yang, Z.-J. Yao, Tetrahedron 2002, 58, 8805.
18. a) H. Arzoumanian, M. Jean, D. Nuel, A. Cabrera, J. L. G. Guiterrez, N. Rosas, Organometallics 1995, 14, 5438.
19. b) R. Shiraki, Y. Shiraga, K. Tadano, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu. 1997, 39, 415.
20. a) M. Kimura, A. Ezoe, M. Mori, K. Iwata, Y. Tamaru, J. Am. Chem. Soc 2006, 128, 8559.
21. b) T. Řezanka, V. M. Dembitsky, Tetrahedron 2001, 57, 8743.
22. c) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971.
23. S. A. King, B. Pipik, A. S. Thompson, A. DeCamp, T. R. Verhoeven, Tetrahedron Lett. 1995, 36, 4563.
24. K. C. Nicolaou, S. E. Webber, Synthesis 1986, 453.
25. R. Ratnayake, V. Karunaratne, B. M. R. Bandara, V. Kumar, J. K. MacLeod, P. Simmonds, J. Nat. Prod. 2001, 64, 376.
26. J. Sheng, Y. L. Wu, Z. J. Yao, Chin. J. Chem. 2002, 20, 692.
27. A. B. Smith, III, G. R. Ott, J. Am. Chem. Soc 1996, 118, 13095.
28. a) J. H. Clark, Chem. Rev. 1980, 80, 429.
29. b) P. C. Montevecchi, M. L. Navacchi, Tetrahedron 2000, 56, 9339.
30. G. Rassu, F. Zanardi, L. Battistinib, G. Casiraghi, Chem. Soc. Rev. 2000, 29, 109.
31. R. H. Young, H. Hart, Chem. Commun. (London) 1967, 827.
32. a) D. L. Boger, C. M. Baldino, J. Am. Chem. Soc. 1993, 115, 11418.
33. b) H. H. Wasserman, R. W. Desimone, D. L. Boger, C. M. Baldino, J. Am. Chem. Soc. 1993, 115, 8457.
34. W. Friedrichsen, Adv. Heterocycl. Chem. 1981, 26, 135.
35. a) B. W. Greatrex, D. K. Taylor, J. Org. Chem. 2004, 69, 2577.
36. b) E. L. Clennan, P. C. Heah, J. Org. Chem. 1981, 46, 4105.