An efficient rearrangement of secondary alkyl S-methyl xanthates by trimethylaluminum (TMA)

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2695-2698

  Barton, Derek H R ^a   Choi, Seung Yong ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

XANTHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029912413     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00339-5     Document Type: Article

References (39)

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20. (b) Harano, K.; Shinohara, I.; Murase, M.; Hisano, T. Heterocycles 1987, 26, 2583. Harano, K.; Kiyonaga, H.; Sugimoto, S-I.; Matsuoka, T.; Hisano, T. Heterocycles 1988, 27, 2327. Harano, K.; Shinohara, I.; Sugimoto, S-I.; Matsuoka, T.; Hisano, T. Chem. Pharm. Bull. 1989, 37(3), 567.
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22. Diana, M. B.; Marchetti, M.; Melloni, G. Tetrahedron: Asymmetry 1995, 6, 1175.
23. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
24. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
25. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
26. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
27. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
28. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
29. Barton, D. H. R.; Zhu, J. Tetrahedron, 1992, 48, 8837. There is precedent for this reaction which we had unintentionally overlooked: Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823. See also Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. Fukutani, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron, Lett. 1984, 25, 5911. Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83. Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto, H. Synthesis, 1986, 130. Maruoka, K.; Yamamoto, H. Tetrahedron, 1988, 44, 5001.
30. 2:C, 72.36; H, 11.56; S, 16.08. Found: C, 72.38; H, 11.46; S, 15.93.
31. 2O; C, 79.14; H, 11.27; S, 7.64. Found: C, 78.91; H, 11.31; S, 7.61.
32. Barton, D. H. R.; Houminer, Y. J. Chem. Soc. Perkin Trans 1. 1972, 919 and references there cited.
33. 1H NMR spectroscopy (w/2).
34. b) Bourdon, R. Bull. Soc. Chim. France, 1962, 844. Bobbio, P. A.; Bobbio, F. O. Ber, 1962, 95, 2747.
35. b) Bourdon, R. Bull. Soc. Chim. France, 1962, 844. Bobbio, P. A.; Bobbio, F. O. Ber, 1962, 95, 2747.
36. Barton, D. H. R.; Cussans, N. J.; Ley, S. V. J. Chem. Soc. Chem. Comm. 1978, 393; J. Chem. Soc. Perkin Trans 1. 1980, 1650.
37. Barton, D. H. R.; Cussans, N. J.; Ley, S. V. J. Chem. Soc. Chem. Comm. 1978, 393; J. Chem. Soc. Perkin Trans 1. 1980, 1650.
38. 2: C, 72.74; H, 10.52; S, 13.39. Found: C, 72.92; H, 10.40; S, 13.11.
39. Contreras, R.; Mendoza, L. Steroids 1979, 34(2), 121.