Synthetic Study of Kedarcidin Chromophore: Advanced Models and Their Chemical Behavior

Synlett

Volumn 1997, Issue 3, 1997, Pages 250-252

  Kawata, Shinji ^a   Yoshimura, Fumihiko ^a   Irie, Jun ^a   Ehara, Hitoshi ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000748262     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-780     Document Type: Article

References (17)

1. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310-10311.
2. Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875-8876.
3. Leet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946-7948; Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson, K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432-8443.
4. Leet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946-7948; Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson, K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432-8443.
5. Yoshida, K.; Minami, Y.; Otani, T.; Tada, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 5253-5256.
6. For reviews of related synthetic studies, see: Lhermitte, H.; Grierson, D.S. Contemp. Org. Synth. 1996, 3, 93-124; Hirama, M. "Synthesis and Chemistry of Neocarzinostalin Analogs," In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2; Lukacs, G. Ed.; Springer-Verlag: Berlin, 1993; pp. 293-329.
7. For reviews of related synthetic studies, see: Lhermitte, H.; Grierson, D.S. Contemp. Org. Synth. 1996, 3, 93-124; Hirama, M. "Synthesis and Chemistry of Neocarzinostalin Analogs," In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol 2; Lukacs, G. Ed.; Springer-Verlag: Berlin, 1993; pp. 293-329.
8. (a) Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851-9853; Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918.
9. (a) Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851-9853; Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918.
10. (b) For synthetic studies of the related highly functionalized cyclopentenones, see: Toyama, K.; Iguchi, S.; Oishi, T.; Hirama, M. Synlett 1995, 1243, and references cited therein.
11. Kong, X.; Grindley, T. B. J. Carbohydr. Chem. 1993, 12, 557-571 and references cited therein.
12. 3 caused a β-elimination to yield an enone.
13. 4, Dess-Martin Oxd., PDC, etc.
14. Sato, I.; Akahori, Y.; Iida, K.; Hirama, M. Tetrahedron Lett. 1996, 37, 5135-5138.
15. For related fragmentation, see: Grob, C. A. Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546; Grob, C. A.; Schiess, P. W. Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15.
16. For related fragmentation, see: Grob, C. A. Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546; Grob, C. A.; Schiess, P. W. Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15.
17. 8 was 6 h.