Synthesis of (±)-madindolines and chemical models. Studies of chemical reactivity

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2337-2340

  McComas, Casey C ^a,b   Perales, Joe B ^a   Van Vranken, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL ADHESION MOLECULE F11; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; MADINDOLINE A; MALEIMIDE DERIVATIVE; MANNICH BASE; MERCAPTAMINE; NERVE CELL ADHESION MOLECULE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STREPTOMYCES; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLIZATION; CYSTEAMINE; INDICATORS AND REAGENTS; INDOLES; MALEIMIDES; MANNICH BASES; MODELS, MOLECULAR; NEURAL CELL ADHESION MOLECULES; STREPTOMYCES; SULFHYDRYL COMPOUNDS;

EID: 0037062902     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026015e     Document Type: Article

References (26)

1. (a) Hayashi, M.; Kim, Y. P.; Takamatsu, S.; Enomoto, A.; Shinose, M.; Takahashi, Y.; Tanaka, H.; Komiyama, K.; Omura, S. J. Antibiot. 1996, 49, 1091-5.
2. (b) Takamatsu, S.; Kim, Y. P.; Enomoto, A.; Hayashi, M.; Tanaka, H.; Komiyama, K.; Omura, S. J. Antibiot. 1997, 50, 1069-72.
3. Omura, S.; Hayashi, M.; Tomoda, H. Pure Appl. Chem. 1999, 71, 1673-81.
4. Moritz, R. L.; Hall, N. E.; Connolly, L. M.; Simpson, R. J. J. Biol. Chem. 2001, 276, 8244-53.
5. Sunazuka, T.; Hirose, T.; Shirahata, T.; Harigaya, Y.; Hayashi, M.; Komiyama, K.; Omura, S.; Smith, A. B., III. J. Am. Chem. Soc. 2000, 122, 2122-3.
6. (a) Hosokawa, S.; Sekiguchi, K.; Hayase, K.; Hirukawa, Y.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 6435-9.
7. (c) Hosokawa, S.; Sekiguchi, K.; Enemoto, M.; Kobayashi, S. Tetrahedron Lett 2000, 41, 6429-33.
8. (c) Hirose, T.; Sunuzaka, T.; Shirata, T.; Yamamoto, D.; Harigaya, Y.; Kuwajima, I.; Omura, S. Org. Lett., 2002, 4, 501-3.
9. (a) Savige, W. E.; Fontana, A. J. Chem. Soc., Chem. Commun. 1976, 600-1.
10. (b) Savige, W. E.; Fontana, A. Int. J. Pept. Protein Res. 1980, 75, 102-12.
11. (c) Wieland, T. B., B.; Zanotti, G. Chem. Pept. Proteins 1989, 4, 95-100.
12. Saito, I.; Morii, T.; Matsugo, S.; Matsuura, T. J. Chem. Soc., Chem. Commun. 1982, 977-9.
13. Miyadera, T.; Kosower, E. M.; Kosower, N. S. J. Med. Chem. 1971, 14.
14. Tressl, R.; Wondrak, G.; Kersten, E.; Rewicki, D. J. Agric. Food Chem. 1994, 42, 2692-7.
15. Smith, I. H.; Wood, E. J.; Casida, J. E. J. Agric. Food Chem. 1982, 30, 598-600.
16. Billington, S.; Mann, J.; Quazi, P.; Alexander, R.; Eaton, M. A. W.; Millar, K.; Millican, A. Tetrahedron 1991, 47, 5231-6.
17. (a) Moore, H. W.; Shelden, H. R. J. Org. Chem. 1968, 33, 4019-24.
18. (b) Moore, H. W.; Weyler, W., Jr.; Shelden, H. R. Tetrahedron Lett. 1969, 3947-50.
19. (c) Weyler, W., Jr.; Pearce, D. S.; Moore, H. W. J. Am. Chem. Soc. 1973, 95, 2603-10.
20. (d) Hamdan, A. J.; Moore, H. W. Heterocycles 1989, 29, 51-6.
21. Cyclopent-4-ene-1,3-diones have been broadly patented for fragrance applications; dione 7 lacks fragrant properties. Isaac, B. O.; Chan, C. O.; Marr, I. M. U.S. Patent 5,407,910, 1995.
22. (a) Hellmann, H.; Opitz, G. α-Aminoalkylierung. Verlag: Weinheim, 1960; p 214.
23. (b) Levchenko, N. K.; Sviridova, A. P.; Segal, G. M.; Torgov, I. V. J. Chem. Res. Miniprint 1978, 5001-27.
24. There is no evidence of the enol in the IR spectrum of diketone 6.
25. Hayashi, T.; Sawamura, M.; Ito, Y. Tetrahedron 1999, 48, 1999-2012.
26. Azidoquinones have been shown to participate in metal-catalyzed intramolecular nitrene-like cycloadditions with tethered dienes. However, Moore rearrangement products were not reported in these studies. Naruta, Yoshinori; Nagai, Naoshi; Arita, Yoshihiro; Maruyama, Kazuhiro J. Org. Chem. 1987, 52, 3956-3967.