Synthesis of an esperamicin core analog with an epoxide trigger

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8683-8686

  Mastalerz, Harold ^b   Doyle, Terrence W ^a,b   Kadow, John F ^b   Vyas, Dolatrai M ^b  

^a Vion Pharmaceuticals Incorporated   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESPERAMICIN DERIVATIVE;

AROMATIZATION; ARTICLE; DRUG SYNTHESIS; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 16144364301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02009-6     Document Type: Article

References (22)

1. 1. a) Kadow, J.; Tun, M.; Vyas, D.; Wittman, M.; Doyle, T. Tetrahedron Lett. 1992, 33 , 1424.
2. b) Zein, N.; Solomon, W.; Casazza, A.M.; Kadow, J.; Krishnan, B.; Tun, M.; Vyas, D.; Doyle, T. Tetrahedron Lett. 1993, 3, 1351.
3. c) Kadow, J.; Cook, D.; Doyle, T.; Langley, D.; Pham, K.; Vyas, D.; Wittman, M. Tetrahedron 1994, 50, 1519.
4. d) Wittman, M.; Kadow, J.; Pham, K.; Leung, K.; Mastalerz, H.; Vyas, D.; Rose, W.; Solomon, W.; Zein, N. Bioorg. Med. Chem. Lett. 1994, 4, 2925.
5. e) Mastalerz, H.; Doyle, T.; Kadow, J.; Leung, K.; Vyas, D. Tetrahedron Lett. 1995, 36, 2925.
6. 2. Tun, M.; Kadow, J. unpublished results.
7. 3. Bergman, R.; Acc. Chem. Res. 1973, 94, 660.
8. 4. For a recent review of enediyne prodrugs, see: Maier, M.E. Synlett 1995, 15.
9. 5. For a recent review on dynemicin, see: Konishi, M.; Oki, T., Dynemicin. In Enediyne Antibiotics as Antitumor Agents, Borders, D.; Doyle, T., Eds; Marcel Dekker, Inc: New York, 1995; pp. 301-325.
10. 6. For a recent review on ADEPT, see: Niculescu-Duvaz, I.; Springer, C.; Exp. Opin. Invest. Drugs 1996, 3, 289. For a review of efforts to target the enediyne, calicheamicin, by conjugation to monoclonal antibodies, see: Hinman, L.; Harmann, P.; Upeslacis, J., Preparation of Conjugates to Monoclonal Antibodies. In reference 5, pp. 87-106.
11. 6. For a recent review on ADEPT, see: Niculescu-Duvaz, I.; Springer, C.; Exp. Opin. Invest. Drugs 1996, 3, 289. For a review of efforts to target the enediyne, calicheamicin, by conjugation to monoclonal antibodies, see: Hinman, L.; Harmann, P.; Upeslacis, J., Preparation of Conjugates to Monoclonal Antibodies. In reference 5, pp. 87-106.
12. -).
13. 8. Magnus, P.; Carter, P.; Elliott, J.; Lewis, R.; Harling, J.; Pitterna, T.; Bauta, W.; Fortt, S. J. Am. Chem. Soc. 1992 114, 2544.
14. 9. Stephens, R.; Castro, C. J. Org. Chem. 1963, 28, 3313.
15. 10. Kende, A.S.; Smith, C. Tetrahedron Lett. 1988 29, 4217.
16. 3.
17. 12. We thank Greg Roth and Dan Marshall for information on their approach to the synthesis of compounds related to 16.
18. 13. Farina, V.; Roth, G. Tetrahedron Lett. 1991, 32, 4243.
19. 14. Griffith, W.; Ley, S.; Whitcombe, G.; White, A. J. Chem. Soc., Chem. Commun. 1987, 1625.
20. 15. The configuration of the secondary alcohol was established by NOE experiments.
21. 16. Curphey, T.J. J. Org. Chem. 1979, 44, 2805.
22. 17. For example, i undergoes conversion to ii within 5 hr at rt in EtOH: Nicolaou, K. C.; Smith, A. L.; Wendeborn, S. V.; Hwang, C-K. J. Amer. Chem. Soc. 1991, 113, 3106. (formula presented)