An efficient preparation of peri-hydroxy dihydroquinone derivatives through a Pummerer-type rearrangement of silylene-protected peri-hydroxy aromatic sulfoxides

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7545-7548

  Kita, Yasuyuki ^a   Takeda, Yoshifumi ^a   Iio, Kiyosei ^a   Yokogawa, Kayoko ^a   Takahashi, Kenji ^a   Akai, Shuji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

QUINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030583501     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01713-3     Document Type: Article

References (18)

1. 1. Trost, B. M.; Caldwell, C. G. Tetrahedron Lett., 1981, 22, 4999-5002; Corey, E. J.; Hopkins, P. B. ibid., 1982, 23, 4871-4874.
2. Trost, B. M.; Caldwell, C. G. Tetrahedron Lett., 1981, 22, 4999-5002; Corey, E. J.; Hopkins, P. B. ibid., 1982, 23, 4871-4874.
3. 2. Kita, Y.; Yasuda, H.; Sugiyama, Y.; Fukata, F.; Haruta, J.; Tamura, Y. Tetrahedron Lett., 1983, 24, 1273-1276.
4. 3. Kita, Y.; Yasuda, H.; Tamura, O.; Tamura, Y. Tetrahedron Lett., 1984, 25, 1813-1816; Kita, Y.; Okunaka, R.; Honda, T.; Shindo, M.; Tamura, O. ibid., 1989, 30, 3995-3998; Kita, Y.; Okunaka, R.; Honda, T.; Kondo, M.; Tamura, O.; Tamura, Y. Chem. Pharm. Bull., 1991, 39, 2106-2114.
5. Kita, Y.; Yasuda, H.; Tamura, O.; Tamura, Y. Tetrahedron Lett., 1984, 25, 1813-1816; Kita, Y.; Okunaka, R.; Honda, T.; Shindo, M.; Tamura, O. ibid., 1989, 30, 3995-3998; Kita, Y.; Okunaka, R.; Honda, T.; Kondo, M.; Tamura, O.; Tamura, Y. Chem. Pharm. Bull., 1991, 39, 2106-2114.
6. 3. Kita, Y.; Yasuda, H.; Tamura, O.; Tamura, Y. Tetrahedron Lett., 1984, 25, 1813-1816; Kita, Y.; Okunaka, R.; Honda, T.; Shindo, M.; Tamura, O. ibid., 1989, 30, 3995-3998; Kita, Y.; Okunaka, R.; Honda, T.; Kondo, M.; Tamura, O.; Tamura, Y. Chem. Pharm. Bull., 1991, 39, 2106-2114.
7. 4. Some recent examples, Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864-865; Bols, M. Tetrahedron, 1993, 44, 10049-10060; Evans, D. A.; Calter, M. A. Tetrahedron Lett., 1993, 34, 6871-6874; Chénedé, A.; Perrin, E.; Rekaï, El D.; Sinaÿ, P. Synlett, 1994, 420-422; Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc., 1994, 116, 4697-4718; Shea, K. J.; Gauthier, Jr., D. R. Tetrahedron Lett., 1994, 35, 7311-7314.
8. Some recent examples, Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864-865; Bols, M. Tetrahedron, 1993, 44, 10049-10060; Evans, D. A.; Calter, M. A. Tetrahedron Lett., 1993, 34, 6871-6874; Chénedé, A.; Perrin, E.; Rekaï, El D.; Sinaÿ, P. Synlett, 1994, 420-422; Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc., 1994, 116, 4697-4718; Shea, K. J.; Gauthier, Jr., D. R. Tetrahedron Lett., 1994, 35, 7311-7314.
9. Some recent examples, Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864-865; Bols, M. Tetrahedron, 1993, 44, 10049-10060; Evans, D. A.; Calter, M. A. Tetrahedron Lett., 1993, 34, 6871-6874; Chénedé, A.; Perrin, E.; Rekaï, El D.; Sinaÿ, P. Synlett, 1994, 420-422; Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc., 1994, 116, 4697-4718; Shea, K. J.; Gauthier, Jr., D. R. Tetrahedron Lett., 1994, 35, 7311-7314.
10. Some recent examples, Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864-865; Bols, M. Tetrahedron, 1993, 44, 10049-10060; Evans, D. A.; Calter, M. A. Tetrahedron Lett., 1993, 34, 6871-6874; Chénedé, A.; Perrin, E.; Rekaï, El D.; Sinaÿ, P. Synlett, 1994, 420-422; Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc., 1994, 116, 4697-4718; Shea, K. J.; Gauthier, Jr., D. R. Tetrahedron Lett., 1994, 35, 7311-7314.
11. Some recent examples, Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864-865; Bols, M. Tetrahedron, 1993, 44, 10049-10060; Evans, D. A.; Calter, M. A. Tetrahedron Lett., 1993, 34, 6871-6874; Chénedé, A.; Perrin, E.; Rekaï, El D.; Sinaÿ, P. Synlett, 1994, 420-422; Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc., 1994, 116, 4697-4718; Shea, K. J.; Gauthier, Jr., D. R. Tetrahedron Lett., 1994, 35, 7311-7314.
12. Some recent examples, Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864-865; Bols, M. Tetrahedron, 1993, 44, 10049-10060; Evans, D. A.; Calter, M. A. Tetrahedron Lett., 1993, 34, 6871-6874; Chénedé, A.; Perrin, E.; Rekaï, El D.; Sinaÿ, P. Synlett, 1994, 420-422; Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc., 1994, 116, 4697-4718; Shea, K. J.; Gauthier, Jr., D. R. Tetrahedron Lett., 1994, 35, 7311-7314.
13. 5. Akai, S.; Iio, K.; Takeda, Y.; Ueno, H.; Yokogawa, K.; Kita, Y. J. Chem. Soc., Chem. Commun., 1995, 2319-2320.
14. 6. Similar easy migration of the silyl group from the phenolic hydroxy group into its neighboring benzylic hydroxy group and easy elimination of the benzylic hydroxy group were often observed during anthracycline syntheses. For an example, see; Tamura, Y.; Akai, S.; Kishimoto, H.; Sasho, M.; Kirihara, M.; Kita, Y. Chem. Pharm. Bull., 1988, 36, 3897-3914.
15. 7. This is probably due to insufficient electron-donation and instability of the isopropylidene group compared to the silylene group. A comparison between these two bifunctional protective groups on a Lewis acid-catalyzed Diels-Alder reaction was reported. See, Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. J. Org. Chem., 1983, 48, 3252-3265.
16. 4Si: C, 68.96; H, 8.05. Found: C, 68,59; H, 8.07. All other new compounds, 8a-f, 9b-f, 10, and 11, were fully characterized by spectroscopic means and elemental analysis and/or high resolution mass spectroscopy.
17. 9. The dihydroxy sulfides 6 were readily prepared by the site selective introduction of the phenylthio group into the corresponding p-unsubstituted phenol derivatives and/or by the cycloaddition of the 4-(phenylthio)homophthalic anhydride to the dienophiles. Details will be presented in a forthcoming paper.
18. 2O-pyridine gave the corresponding triacetate in 86% yield from 8f. Two quinone compounds 10 and 11 are interconvertible nearly quantitatively.