Synthetic studies on bengazoles of marine sponge origin. Synthesis of the core bis-oxazole fragments

Synlett

Volumn , Issue 9, 1998, Pages 1022-1024

  Chittari, Pabba ^a   Hamada, Yasumasa ^b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0142020462     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1852     Document Type: Article

References (28)

1. a) Adamczeski, M.; Quinoà, E.; Crews, P. J. Am. Chem. Soc. 1988, 110, 1598.
2. b) Crews, P.; Mathews, T. R.; Emilo, Q.; Adamczeski, M. U. S. Patent 4,785,012 (1988).
3. c) Rodriguez, J.; Nieto, R. M.; Crews, P. J. Nat. Prod. 1993, 56, 2034
4. d) Searle, P. A.; Richter, R. K; Molinski, T. F. J. Org. Chem. 1996, 61, 4073.
5. e) Molinski, T. F. J. Nat. Prod. 1993, 56, 1.
6. f) Rudi, A,; Kashman, Y.; Benayahu, Y.; Schleyer, M. J. Nat. Prod. 1994, 57, 829.
7. Shafer, C. M.; Molinski, T. F. Tetrahedron Lett. 1998, 39, 2903.
8. Presented in part at the 117th Annual Meeting of the Pharmaceutical Society of Japan (Tokyo), March 26-28, 1997, Abstracts 2, p.16
9. the 118th Annual Meeting of the Pharmaceutical Society of Japan (Kyoto), March 31-April 2, 1998, Abstracts 2, p.47.
10. (a) Schöllkopf, U.; Schröder, R. Angew. Chem. Int. Ed. Engl. 1971,10, 333.
11. (b) Henneke, K. W.; Schöllkopf, U.; Neudecker, T. Liebigs Ann. Chem. 1979, 1370.
12. Hodges, J. C.; Patt, W. C.; Connolly, C. J J. Org. Chem. 1991, 56, 449 and references therein.
13. Vedejs, E.; Monahan, S. D. J. Org. Chem. 1996, 61, 5192.
14. Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Synlett 1998, 35.
15. (a) Brown, H. C.; Chandrasekharan, J.; Ramachandran P. V. J. Am. Chem. Soc. 1988, 110, 1539.
16. (b) Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 1992, 48, 7251.
17. a) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861.
18. b) Itsuno, S.; Sakurai, Y.; Ito, K.; Hirao, A.; Nakahama, S. Bull. Chem. Soc. Jpn. 1987, 60, 395.
19. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 5675.
20. Masui, M.; Shioiri, T. Synlett 1997, 273.
21. Quallich, G. J.; Woodall, T. M. Tetrahedron Lett. 1993, 34, 4145.
22. a) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
23. b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
24. Ohtani I,; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
25. 13 (Chemical Equation Presented)
26. 2), 6.99 (s, 1H, CH), 7.34-7.43 (m, 6H, ArH), 7.47 (s, 1H, CH), 7.65 (m, 4H, ArH), 7.83 (s. 1H, CH).
27. (a) Barton, D. H. R.; McCombie, S.W, J. 'Chem. Soc., Perkin Trans. 1 1975, 1574.
28. (b) Barton, D. H. R.; Jang D. O.; Jaszberenyi, J. C. J. Org. Chem. 1993, 58, 6838.