An efficient synthesis of peri-hydroxy aromatic compounds: A strong base-induced [4+2]cycloaddition of 4-phenylthio-substituted homophthalic anhydrides with various sulfinyl-substituted dienophiles

Synlett

Volumn , Issue 3, 1998, Pages 292-294

  Kita, Yasuyuki ^a   Iio, Kiyosei ^a   Okajima, Akiko ^a   Takeda, Yoshifumi ^a   Kawaguchi, Ken Ichi ^a   Whelan, Brendan A ^a   Akai, Shuji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002596499     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1642     Document Type: Article

References (29)

1. a) Thompson, R. H. Naturally Occurring Quinones; Academic Press: New York, 1971;
2. b) Arcamone, F. Topics in Antibiotics Chemistry; Sammes, P. G., Ed.; Halstead Press: New York; 1978; Vol. 2;
3. c) Oki, T.; Takeuchi, T. Yuki Gosei Kagaku Kyokaishi 1982, 40, 2-19;
4. d) Tamura, Y.; Kita, Y. Yuki Gosei Kagaku Kyokaishi ibid. 1988, 46, 205-217;
5. e) Kita, Y.; Takeda, Y. Kagaku to Kogyo 1997, 71, 298-309.
6. a) Pandey, R. C.; Toussaint, M. W.; Stroshane, R. M.; Kalita, C. C.; Aszalos, A. A.; Garretson, A. L.; Wei, T. T.; Byrne, K. M.; Geoghegan, R. F., Jr.; White, R. J. J. Antibiot. 1981, 34, 1389-1401;
7. b) Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839-11849 and references cited therein.
8. a) Akai, S.; Takeda, Y.; Iio, K.; Yoshida, Y.; Kita, Y. J. Chem. Soc., Chem. Commun. 1995, 1013-1014;
9. b) Kita, Y.; Takeda, Y.; Iio, K.; Yokogawa, K.; Takahashi, K.; Akai, S. Tetrahedron Lett. 1996, 37, 7545-7548;
10. c) Akai, S.; Takeda, Y.; Iio, K.; Takahashi, K.; Fukuda, N.; Kita, Y. J. Org. Chem. 1997, 62, 5526-5536;
11. d) Kita, Y.; Takeda, Y.; Matsugi, M.; Iio, K.; Gotanda, K.; Murata, K.; Akai, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 1529-1531.
12. a) Kita, Y.; Okuno, T.; Egi, M.; Iio, K.; Takeda, Y.; Akai, S. Synlett 1994, 1039-1040;
13. b) Kita, Y.; Takeda, Y.; Okuno, T.; Egi, M.; Iio, K.; Kawaguchi, K.; Akai, S. Chem. Pharm. Bull. in press.
14. a) Kita, Y.; Okunaka, R.; Honda, T.; Shindo, M.; Tamura, O. Tetrahedron Lett. 1989, 30, 3995-3998;
15. b) Kita, Y.; Okunaka, R.; Honda, T.; Kondo, M.; Tamura, O.; Tamura, Y. Chem. Pharm. Bull. 1991, 39, 2106-2114;
16. c) Akai, S.; Iio, K.; Takeda, Y.; Ueno, H.; Kita, Y. Synlett 1997, 310-312.
17. a) Tamura, Y.; Sasho, M.; Nakagawa, K.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473-478;
18. b) Tamura, Y.; Fukata, F.; Sasho, M.; Tsugoshi, T.; Kita, Y. J. Org. Chem. ibid. 1985, 50, 2273-2277.
19. X = Cl, Br; a) Banville, J.; Grandmaison, J. -L.; Lang, G.; Brassard, P. Can. J. Chem. 1974, 52, 80-87;
20. b) Cameron, D. W.; Feutrill, G. I.; Griffiths, P. G.; Hodder, D. J. J. Chem. Soc., Chem. Commun. 1978, 688-689;
21. c) Roberge, G.; Brassard, P. J. Org. Chem. 1981, 46, 4161-4166;
22. d) Echavarren, A.; Prados, P.; Fariña, F. Tetrahedron 1984, 40, 4561-4567;
23. e) Bauman, J. G.; Hawley, R. C.; Rapoport, H. J. Org. Chem. 1985, 50, 1569-1573.
24. X = SOPh; a) Paquette, L. A.; Moerck, R. E.; Harirchian, B.; Magnus, P. D. J. Am. Chem. Soc. 1978, 100, 1597-1599;
25. b) Danishefsky, S.; Harayama, T.; Singh, R. K. J. Am. Chem. Soc. ibid. 1979, 101, 7008-7012;
26. c) Kaydos, J. A.; Smith, D. L. J. Org. Chem. 1983, 48, 1096-1099;
27. d) Kraus, G. A.; Woo, S. H. J. Org. Chem. ibid. 1986, 51, 114-116.
28. 4S: C, 74.98; H, 5.03; S, 6.67. Found: C, 74.63; H, 5.08; S, 6.59.
29. 1H NMR, HRMS) and/or elemental analyses for unknown compounds (2, 3b, 4d, 5b, 7-12) were obtained.