Actuating Cycloaromatization of a Bicyclo[7.3.1]enediyne by Annelation: An Example of Inverse Dependence on Bridge Atom Hybridization

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 470-473

  Nantz, Michael H ^a   Moss, David K ^a   Spence, John D ^a   Olmstead, Marilyn M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Annulation; Cycloaromatizations; Enediynes; Kinetics; Spiro compounds

Indexed keywords

ANNELATION; BICYCLO[7.3.1]ENEDIYNE; CHEMICAL ANALYSIS; CYCLOAROMATIZATION;

EID: 0032473574     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<470::aid-anie470>3.3.co;2-h     Document Type: Article

References (43)

1. a) M. D. Lee, T. S. Dunne, M. M. Siegel, C. C. Chang, G. O. Morton, D. B. Borders, J. Am. Chem. Soc. 1987, 109, 3464, 3466;
2. b) J. Golik, J. Clardy, G. Dubay, G. Groenwold, H. Kawaguchi, M. Konishi, B. Krishnan, H. Ohkum, K. Saitoh, T. W. Doyle, ibid. 1987, 109, 3461, 3462.
3. For reviews of enediyne chemistry and biology, see a) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; b) M. E. Maier, Synlett 1995, 13; c) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; d) Enediyne Antibiotics as Antitumor Agents (Eds.: T. W. Doyle, D. B. Borders), Marcel Dekker, New York, 1994.
4. For reviews of enediyne chemistry and biology, see a) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; b) M. E. Maier, Synlett 1995, 13; c) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; d) Enediyne Antibiotics as Antitumor Agents (Eds.: T. W. Doyle, D. B. Borders), Marcel Dekker, New York, 1994.
5. For reviews of enediyne chemistry and biology, see a) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; b) M. E. Maier, Synlett 1995, 13; c) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; d) Enediyne Antibiotics as Antitumor Agents (Eds.: T. W. Doyle, D. B. Borders), Marcel Dekker, New York, 1994.
6. For reviews of enediyne chemistry and biology, see a) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; b) M. E. Maier, Synlett 1995, 13; c) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; d) Enediyne Antibiotics as Antitumor Agents (Eds.: T. W. Doyle, D. B. Borders), Marcel Dekker, New York, 1994.
7. For reviews of enediyne chemistry and biology, see a) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; b) M. E. Maier, Synlett 1995, 13; c) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; d) Enediyne Antibiotics as Antitumor Agents (Eds.: T. W. Doyle, D. B. Borders), Marcel Dekker, New York, 1994.
8. a) K. C. Nicolaou, C. W. Hummel, C. N. Pitsinos, M. Nakada, A. L. Smith, K. Shibayama, H. Saimoto, J. Am. Chem. Soc. 1992, 114, 10082;
9. b) K. C. Nicolaou, C. W. Hummel, M. Nakada, K. Shibayama, C. N. Pitsinos, H. Saimoto, Y. Mizuno, K.-U. Baldenius, A. L. Smith, ibid. 1993, 115, 7625;
10. c) S. A. Hitchcock, M. Y. Chu-Moyer, S. H. Boyer, S. H. Olson, S. J. Danishefsky, ibid. 1995, 117, 5750.
11. For syntheses of calicheamicinone and calicheamicin analogues, see ref. [2] and D. L. J. Clive, Y. Bo, Y. Tao, S. Daigneault, Y.-J. Wu, G. Meignan, J. Am. Chem. Soc. 1996, 118, 4904.
12. a) R. R. Jones, R. G. Bergman, J. Am. Chem. Soc. 1972, 94, 660;
13. b) R. G. Bergman, Acc. Chem. Res. 1973, 6, 25;
14. c) T. P. Lockhart, P. B. Comita, R. G. Bergman, J. Am. Chem. Soc. 1981, 103, 4082;
15. d) see also; N. Darby, C. U. Kim, J. A. Salaun, K. W. Shelton, S. Takada, S. Masamune, J. Chem. Soc. Chem. Commun. 1971, 1516.
16. P. Magnus, R. T. Lewis, J. C. Huffman, J. Am. Chem. Soc. 1988, 110, 6921.
17. -1; see a) P. Magnus, S. Fortt, T. Pitterna, J. P. Snyder, J. Am. Chem. Soc. 1990, 112, 4986; b) P. Magnus, P. Carter, J. Elliott, R. Lewis, J. Harling, T. Pitterna, W. E. Bauta, S. Fortt, ibid. 1992, 114, 2544.
18. -1; see a) P. Magnus, S. Fortt, T. Pitterna, J. P. Snyder, J. Am. Chem. Soc. 1990, 112, 4986; b) P. Magnus, P. Carter, J. Elliott, R. Lewis, J. Harling, T. Pitterna, W. E. Bauta, S. Fortt, ibid. 1992, 114, 2544.
19. Enediyne 2 undergoes complete cycloaromatization at 20 °C within 30 min. [6]
20. For examples of intramolecular triggering of bicyclo[7.3.1]enediynes. see a) J. N. Haseltine, S. J. Danishefsky, G. Schulte, J. Am. Chem. Soc. 1989, 111, 7638; b) J. N. Haseltine, S. J. Danishefsky, J. Org. Chem. 1990, 55, 2576; c) S. J. Danishefsky, M. D. Shair, ibid. 1996, 61, 16.
21. For examples of intramolecular triggering of bicyclo[7.3.1]enediynes. see a) J. N. Haseltine, S. J. Danishefsky, G. Schulte, J. Am. Chem. Soc. 1989, 111, 7638; b) J. N. Haseltine, S. J. Danishefsky, J. Org. Chem. 1990, 55, 2576; c) S. J. Danishefsky, M. D. Shair, ibid. 1996, 61, 16.
22. For examples of intramolecular triggering of bicyclo[7.3.1]enediynes. see a) J. N. Haseltine, S. J. Danishefsky, G. Schulte, J. Am. Chem. Soc. 1989, 111, 7638; b) J. N. Haseltine, S. J. Danishefsky, J. Org. Chem. 1990, 55, 2576; c) S. J. Danishefsky, M. D. Shair, ibid. 1996, 61, 16.
23. a) J. D. Spence, L. E. Lowrie, M. H. Nantz, Tetrahedron Lett. 1995, 36, 5499;
24. b) J. D. Spence, J. K. Wyatt, D. M. Bender, D. K. Moss, M. H. Nantz, J. Org. Chem. 1996, 61, 4014.
25. N. C. Yang, R. A. Finnegan, J. Am. Chem. Soc. 1958, 80, 5845.
26. The epoxidation selectivity decreased to 2:1 when the corresponding C(7) (tert-butyldiphenylsilyloxy)methyl derivative of 5 was treated under identical conditions, suggesting a shielding of the enone face syn to C(7).
27. W. Nagata, M. Yoshioka, Tetrahedron Lett. 1966, 1913.
28. a) T. Imamoto, Y. Sugiura, N. Takiyama, Tetrahedron Lett. 1984, 25, 4233;
29. b) For an experimental procedure to prepare anhydrous cerium chloride, see T. Imamoto in Comprehensive Organic Synthesis Vol. 1 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford. 1991, p. 231.
30. M. D. Shair, T. Yoon, S. J. Danishefsky, J. Org. Chem. 1994, 59, 3755.
31. a) H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. 1984, 96, 720; Angew. Chem. Int. Ed. Engl. 1984, 23, 727;
32. a) H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. 1984, 96, 720; Angew. Chem. Int. Ed. Engl. 1984, 23, 727;
33. b) T. Nishikawa, S. Shibuya, S. Hosokawa, M. Isobe, Synlett 1994, 485.
34. T. N. Mitchell, A. Amamria, H. Killing, D. Rutschow, J. Organomet. Chem. 1986, 304, 257.
35. 1H NMR spectrum of this material was identical to the spectrum that was obtained from freshly purifed 3.
36. K. C. Nicolaou, G. Zuccarello, C. Riemer, V. A. Estevez, W.-M. Dai, J. Am. Chem. Soc. 1992, 114, 7360.
37. [7] is 3.39 Å. The calculations were performed with the program PC Model 4.4 from Serena Software.
38. The influence of benzannelation on the enediyne moiety has been documented, see K. C. Nicolaou, W.-M. Dai, Y. P. Hong, S.-C. Tsay, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1993, 115, 7944.
39. J. P. Snyder, J. Am. Chem. Soc. 1990, 112, 5367.
40. a) M. E. Maier, T. Brandstetter, Tetrahedron 1994, 50, 1435;
41. b) M. E. Maier, D. Langenbacher, Synlett 1994, 713.
42. 2) = 1.066. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallogrphic Data Centre as supplementary publication no. CCDC-100780. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; E-mail: deposit@chemcrys.cam.ac.uk).
43. -1. Full theoretical calculations will be reported in a forthcoming account of this work.