Synthesis and X-ray crystal structure of (-)-calicheamicinone

Tetrahedron

Volumn 55, Issue 11, 1999, Pages 3277-3290

  Clive, Derrick L J ^a   Bo, Yunxin ^a   Selvakumar, Natesan ^a   McDonald, Robert ^a   Santarsiero, Bernard D ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b Molecular Structure Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALICHEAMICIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS;

EID: 0033104471     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01140-5     Document Type: Article

References (35)

1. (a) Preliminary communication: Clive, D. L. J.; Selvakumar, N. J. Chem. Soc., Chem. Commun. 1996, 2543.
2. Prior syntheses: (b) Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimoto, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612.
3. (c) Aiyer, J. Hitchcock, S. A.; Denhart, D.; Liu, K. K.-C; Danishefsky, S. J.; Crothers, D. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 855.
4. For a comprehensive list of references to the mechanism of antitumor action of calicheamicin, see reference 3.
5. (a) Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1996, 118, 4904.
6. (b) Full paper: Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1998, 120, 10332.
7. Cf. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
8. Clive, D. L. J.; Keshava Murthy, K. S.; Wee, A. G. H.; Prasad, J. S.; da Silva, G. V. J.; Majewski, M.; Anderson, P. C.; Evans, C. F.; Haugen, R. D.; Heerze, L. D., Barrie, J. R. J. Am. Chem. Soc. 1990, 112, 3018.
9. E.g., Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. Whitesell, J. K. Chem. Rev. 1992, 92, 953, and references therein. Oppolzer, W.; Kurth, M.; Reichlin, D.; Chapuis, C.; Mohnhaupt, M.; Moffatt, F. Helv. Chim. Acta 1981, 64, 2802.
10. E.g., Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. Whitesell, J. K. Chem. Rev. 1992, 92, 953, and references therein. Oppolzer, W.; Kurth, M.; Reichlin, D.; Chapuis, C.; Mohnhaupt, M.; Moffatt, F. Helv. Chim. Acta 1981, 64, 2802.
11. E.g., Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. Whitesell, J. K. Chem. Rev. 1992, 92, 953, and references therein. Oppolzer, W.; Kurth, M.; Reichlin, D.; Chapuis, C.; Mohnhaupt, M.; Moffatt, F. Helv. Chim. Acta 1981, 64, 2802.
12. Ort, O. Org. Synth. 1987, 65, 203.
13. Whitesell, J. K.; Bhattacharya, A.; Buchanan, C. M.; Chen, H. H.; Deyo, D.; James, D.; Liu, C.-L.; Minton, M. A. Tetrahedron 1986, 42, 2993.
14. Cf. Whitesell, J. K.; Liu, C.-L.; Buchanan, C. M.; Chen, H.-H.; Minton, M. A. J. Org. Chem. 1986, 51, 551.
15. Rosini, G.; Ballini, R.; Sorrenti, P. Synthesis 1983, 1014.
16. Cf. Melton, J.; McMurry, J. E. J. Org. Chem. 1975, 40, 2138.
17. Cf. Corey, E. J.; Jones, G. B. J. Org. Chem. 1992, 57, 1028.
18. Available from our earlier work with racemic compounds (see reference 3).
19. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
20. Kunz, H.; Unverzagt, C. Angew. Chem., Int. Edn. Engl. 1984, 23, 436.
21. Cf. Dayagi, S.; Degani, Y. In The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience: New York, 1970; p 61.
22. The acid exits in equilibrium with epimeric hydroxy lactones (i.e. replacement of Br in structure 35 by OH).
23. Cf. (a) Harpp, D. N.; Ash, D. K. Int. J. Sulfur Chem. Part A 1971, 1, 57.
24. (b) Sullivan, A. B.; Boustany, K. Int. J. Sulfur Chem. Part A 1971, 1, 207.
25. (c) Harpp, D. N.; Ash, D. K. Int. J. Sulfur Chem. Part A 1971, 1, 211.
26. Haseltine, J. N.; Paz Cabal, M.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850.
27. Reaction takes 8 h but, in the racemic series, where the progress of the reaction was also monitored by TLC, reaction took 16 h.
28. The atomic coordinates have been submitted to the Cambridge Crystallographic Data Centre.
29. We searched for carbamates in which the C-N-C(O)-O unit was in a chain or in a ring that was at least seven-membered.
30. Clive, D. L. J.; Wickens, P. L.; Sgarbi, P. W. M. J. Org. Chem. 1996, 61, 7426.
31. D-16.9 (c 2.2, EtOH).
32. Zhinkin, D. Ya.; Mal'nova, G. N.; Gorislavskaya, Zh. V. J. Gen. Chem. USSR 1968, 38, 2702.
33. Cf. Oppolzer, W.; Kurth, M.; Reichlin, D.; Moffatt, F. Tetrahedron Lett. 1981, 22, 2545.
34. The procedure used with the corresponding racemic compound was followed.
35. 2).