Collect. Czech. Chem. Commun. 2004, 69, 945-965
https://doi.org/10.1135/cccc20040945

Electronic Effects on the Bergman Cyclisation of Enediynes. A Review

Michael Klein, Thomas Walenzyk and Burkhard König*

Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany

References

1a. Konishi M., Ohkuma H., Saitoh K., Kawaguchi H., Golik J., Dubay G., Groenewald G., Krishnan B., Doyle T. W.: J. Antibiot. 1985, 38, 1605. <https://doi.org/10.7164/antibiotics.38.1605>
1b. Golik J., Clardy J., Dubay G., Groenewald G., Kawaguchi H., Konishi M., Krishnan B., Ohkuma H., Saitoh K., Doyle T. W.: J. Am. Chem. Soc. 1987, 109, 3461. <https://doi.org/10.1021/ja00245a048>
1c. Golik J., Dubay G., Groenewald G., Kawaguchi H., Konishi M., Krishnan B., Ohkuma H., Saitoh K., Doyle T. W.: J. Am. Chem. Soc. 1987, 109, 3462. <https://doi.org/10.1021/ja00245a049>
1d. Golik J., Wong H., Vyas D. M., Doyle T. W.: Tetrahedron Lett. 1989, 30, 2497. <https://doi.org/10.1016/S0040-4039(01)80434-2>
2a. Lee M. D., Dunne T. S., Siegel M. M., Chang C. C., Morton G. O., Borders D. B.: J. Am. Chem. Soc. 1987, 109, 3464. <https://doi.org/10.1021/ja00245a050>
2b. Lee M. D., Dunne T. S., Chang C. C., Ellestad G. A., Siegel M. M., Morton G. O., McGahren W. J., Borders D. B.: J. Am. Chem. Soc. 1987, 109, 3466. <https://doi.org/10.1021/ja00245a051>
2c. Lee M. D., Manning J. K., Williams D. R., Kuck N. A., Testa R. T., Borders D. B.: J. Antibiot. 1989, 42, 1070. <https://doi.org/10.7164/antibiotics.42.1070>
2d. Maiese W. M., Lechevalier M. P., Lechevalier H. A., Korshalla J., Kuck N. A., Fantini A., Wildey M. J., Thomas J., Greenstein M.: J. Antibiot. 1989, 42, 558. <https://doi.org/10.7164/antibiotics.42.558>
2e. Lee M. D., Dunne T. S., Chang C. C., Siegel M. M., Morton G. O., Ellestadt G. A., McGahren W. J., Borders D. B.: J. Am. Chem. Soc. 1992, 114, 985. <https://doi.org/10.1021/ja00029a030>
2f. Thorson J. S., Sievers E. L., Ahlert J., Shepard E., Whitwam R. E., Onwueme K. C., Ruppen M.: Curr. Pharm. Des. 2000, 6, 1841. <https://doi.org/10.2174/1381612003398564>
3a. Konishi M., Ohkuma H., Matsumoto K., Tsuno T., Kamei H., Miyaki T., Oki T., Kawaguchi H., VanDuyne G. D., Clardy J.: J. Antibiot. 1989, 42, 1449. <https://doi.org/10.7164/antibiotics.42.1449>
3b. Konishi M., Ohkuma H., Tsuno T., Oki T., VanDuyne G. D., Clardy J.: J. Am. Chem. Soc. 1990, 112, 3715. <https://doi.org/10.1021/ja00165a097>
3c. Maier M. E., Bosse F., Niestroj A. J.: Eur. J. Org. Chem. 1999, 1. <https://doi.org/10.1002/(SICI)1099-0690(199901)1999:1<1::AID-EJOC1>3.0.CO;2-D>
4. Borders D. B., Doyle T. W.: Enediyne Antibiotics as Antitumor Agents. Marcel Dekker, New York 1995.
5. For the use of enediyne cyclisation products as radical polymerisation initiators, see: Rule J. D., Wilson S. R., Moore J. S.: J. Am. Chem. Soc. 2003, 125, 12992.
6a. Jones R. R., Bergman R. G.: J. Am. Chem. Soc. 1972, 94, 660. <https://doi.org/10.1021/ja00757a071>
6b. Bergman R. G.: Acc. Chem. Res. 1973, 6, 25. <https://doi.org/10.1021/ar50061a004>
7. Roth W. R., Hopf H., Horn C.: Chem. Ber. 1994, 127, 1765. <https://doi.org/10.1002/cber.19941270929>
8. Prall M., Wittkopp A., Schreiner P. R.: J. Phys. Chem. A 2001, 105, 9265. <https://doi.org/10.1021/jp0028002>
9a. Schreiner P. R., Prall M., Lutz V.: Angew. Chem. 2003, 115, 5935. <https://doi.org/10.1002/ange.200351195>
9b. Schreiner P. R., Prall M., Lutz V.: Angew. Chem., Int. Ed. 2003, 46, 5757. <https://doi.org/10.1002/anie.200351195>
10a. Myers A. G., Kuo E. Y., Finney N. S.: J. Am. Chem. Soc. 1989, 111, 8057. <https://doi.org/10.1021/ja00202a079>
10b. Saito K., Watanabe T., Takahashi K.: Chem. Lett. 1989, 2099. <https://doi.org/10.1246/cl.1989.2099>
11. Schmittel M., Strittmatter M., Kiau S.: Tetrahedron Lett. 1995, 36, 4975. <https://doi.org/10.1016/0040-4039(95)00937-8>
12a. Tykwinski R. R.: Chem. Commun. 1999, 905. <https://doi.org/10.1039/a900910h>
12b. Snyder J. P.: J. Am. Chem. Soc. 1990, 122, 5367. <https://doi.org/10.1021/ja00169a064>
12c. Schreiner P. R.: Chem. Commun. 1998, 4, 483. <https://doi.org/10.1039/a707836f>
12d. Schreiner P. R.: J. Am. Chem. Soc. 1998, 120, 4184. <https://doi.org/10.1021/ja973591a>
12e. Nicolaou K. C., Zuccarello G., Ogawa Y., Schweiger E. J., Kumazawa T.: J. Am. Chem. Soc. 1988, 110, 4866. <https://doi.org/10.1021/ja00222a077>
12f. Mita T., Kawata S., Hirama M.: Chem. Lett. 1998, 959. <https://doi.org/10.1246/cl.1998.959>
12g. Semmelhack M. F., Neu T., Foubelo F.: J. Org. Chem. 1994, 59, 5038. <https://doi.org/10.1021/jo00096a057>
13. For a recent example of conformational control in enediyne activation, see: Semmelhack M. F., Wu L., Pascal R. A., Ho D. M.: J. Am. Chem. Soc. 2003, 125, 10496.
14a. Basak A., Shain J. C.: Tetrahedron Lett. 1998, 39, 3029. <https://doi.org/10.1016/S0040-4039(98)00325-6>
14b. Basak A., Shain J. C., Khamrai U. K., Rudra K. R.: J. Chem. Soc., Perkin Trans. 1 2000, 1955. <https://doi.org/10.1039/b000963f>
14d. Warner B. P., Millar S. P., Broene R. D., Buchwald S. L.: Science 1995, 269, 814. <https://doi.org/10.1126/science.269.5225.814>
14e. König B., Pitsch W.: J. Org. Chem. 1996, 61, 4258. <https://doi.org/10.1021/jo9600971>
14f. Kraka E., Cremer D.: J. Am. Chem. Soc. 2000, 122, 8245. <https://doi.org/10.1021/ja001017k>
14g. O’Connor J. M., Friese S. J., Tichenor M.: J. Am. Chem. Soc. 2002, 124, 3506. <https://doi.org/10.1021/ja017873t>
15a. Evenzahav A., Turro N. J.: J. Am. Chem. Soc. 1998, 120, 1835. <https://doi.org/10.1021/ja9722943>
15b. Alabugin I. V., Kovalenko S. V.: J. Am. Chem. Soc. 2002, 124, 9052. <https://doi.org/10.1021/ja026630d>
16. For a recent example of photochemical DNA cleavage using metalloenediynes, see: Benites P. J., Holmberg R. C., Rawat D. S., Kraft B. J., Klein L. J., Peters G. D., Thorp H. H., Zaleski J. M.: J. Am. Chem. Soc. 2003, 125, 6434.
17. Schmittel M., Maywald M.: Chem. Commun. 2001, 155. <https://doi.org/10.1039/b007811p>
18. Basak A., Mandal S., Bag S. S.: Chem. Rev. 2003, 103, 4077. <https://doi.org/10.1021/cr020069k>
19. For the effect of pentamethylcyclopentadienyl ruthenium cation on the reactivity of benzo-fused enediynes, see: O’Connor J. M., Lee L. I., Ganzel P.: J. Am. Chem. Soc. 2000, 122, 12057.
20. Bhattacharyya S., Clark A. E., Pink M., Zaleski J. M.: Chem. Commun. 2003, 1156. <https://doi.org/10.1039/b301690k>
21. Koga N., Morokuma K.: J. Am. Chem. Soc. 1991, 113, 1907. <https://doi.org/10.1021/ja00006a006>
22a. Nagata R., Yamanaka H., Okazaki E., Saito I.: Tetrahedron Lett. 1989, 30, 4995. <https://doi.org/10.1016/S0040-4039(01)80564-5>
22b. Myers A. G., E. Kuo Y., Finney N. S.: J. Am. Chem. Soc. 1989, 111, 8057. <https://doi.org/10.1021/ja00202a079>
23. Schmittel M., Kiau S.: Chem. Lett. 1995, 953. <https://doi.org/10.1246/cl.1995.953>
24. Galbraith J. M., Schreiner P. R., Harris N., Wie W., Shaik S.: Chem. Eur. J. 2000, 6, 1446. <https://doi.org/10.1002/(SICI)1521-3765(20000417)6:8<1446::AID-CHEM1446>3.0.CO;2-I>
25. Stahl F., Moran D., Schleyer P. von Ragué, Prall M., Schreiner P. R.: J. Org. Chem. 2002, 67, 1453. <https://doi.org/10.1021/jo015728s>
26. Schreiner P. R.: J. Am. Chem. Soc. 1998, 120, 4184. <https://doi.org/10.1021/ja973591a>
27. König B., Pitsch W., Klein M., Vasold R., Prall M., Schreiner P. R.: J. Org. Chem. 2001, 66, 1742. <https://doi.org/10.1021/jo001417q>
28a. Semmelhack M. F., Neu T., Foubelo F.: J. Org. Chem. 1994, 59, 5038. <https://doi.org/10.1021/jo00096a057>
28b. Boger D. L., Zhou J.: J. Org. Chem. 1993, 58, 3018. <https://doi.org/10.1021/jo00063a019>
28c. Just G., Singh R.: Tetrahedron Lett. 1990, 31, 185.
28c. The half-live times cannot be compared to those of the propargylic alcohol 15 on account of different experimental conditions (i.e. temperature).
29. Semmelhack M. F., Gu Y., Ho D. M.: Tetrahedron Lett. 1997, 38, 5586. <https://doi.org/10.1016/S0040-4039(97)01263-X>
30. Prall M., Wittkopp A., Fokin A. A., Schreiner P. R.: J. Comput. Chem. 2001, 22, 1605. <https://doi.org/10.1002/jcc.1114>
31a. Wenk H. H., Balster A., Sander W., Hrovat D. A., Borden W. T.: Angew. Chem. 2001, 113, 2356. <https://doi.org/10.1002/1521-3757(20010618)113:12<2356::AID-ANGE2356>3.0.CO;2-S>
31b. Wenk H. H., Balster A., Sander W., Hrovat D. A., Borden W. T.: Angew. Chem., Int. Ed. 2001, 40, 2295. <https://doi.org/10.1002/1521-3773(20010618)40:12<2295::AID-ANIE2295>3.0.CO;2-W>
32. Nath M., Huffman J. C., Zaleski J. M.: J. Am. Chem. Soc. 2003, 125, 11484. <https://doi.org/10.1021/ja0302782>
33. Bowles D. M., Anthony J. E.: Org. Lett. 2000, 2, 85. <https://doi.org/10.1021/ol991254w>
34. Witulski B., Stengel T.: Angew. Chem., Int. Ed. Engl. 1998, 37, 489. <https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<489::AID-ANIE489>3.0.CO;2-N>
35. Klein M.: Ph.D. Thesis. University of Regensburg, Regensburg 2003.
36. Maier M. E., Greiner B.: Liebigs Ann. Chem. 1992, 855. <https://doi.org/10.1002/jlac.1992199201140>
37. Jones G., Plourde G. W., Jr.: Org. Lett. 2000, 2, 1757. <https://doi.org/10.1021/ol0059394>
38. Jones G. B., Warner P. M.: J. Am. Chem. Soc. 2001, 123, 2134. <https://doi.org/10.1021/ja0033032>
39. Plourde G. W., Jr., Warner P. M., Parrish D. A., Jones G. B.: J. Org. Chem. 2002, 67, 5369. <https://doi.org/10.1021/jo025763e>
40. Nicolaou K. C., Dai W.-D., Hong Y. P., Tsay S.-C., Baldige K. K., Siegel J. S.: J. Am. Chem. Soc. 1993, 115, 7944. <https://doi.org/10.1021/ja00071a003>
41. Basak A., Shain J. C., Khamrai U. K., Rudra K. R., Basak A.: J. Chem. Soc., Perkin Trans. 1 2000, 1955. <https://doi.org/10.1039/b000963f>
42. For another example of enediyne stabilisation by benzo-fusion, see: Boger D. L., Zhou J.: J. Org. Chem. 1993, 58, 3018.
43. Semmelhack M. F., Neu T., Foubelo F.: J. Org. Chem. 1994, 59, 5038. <https://doi.org/10.1021/jo00096a057>
44a. Roth W. R., Hopf H., Wasser T., Zimmermann H., Werner C.: Liebigs Ann. 1996, 1691. <https://doi.org/10.1002/jlac.199619961030>
44b. Wenthold P. G., Squires R. R.: J. Am. Chem. Soc. 1994, 116, 6401. <https://doi.org/10.1021/ja00093a047>
44c. Wisniewski Grissom J., Calkins T. L., McMillen H. A., Jiang Y.: J. Org. Chem. 1994, 59, 5833. <https://doi.org/10.1021/jo00098a055>
45. Jones G. B., Warner P. M.: J. Am. Chem. Soc. 2001, 123, 2134. <https://doi.org/10.1021/ja0033032>
46. Choy N., Kim C.-S., Ballestero C., Artigas L., Diez C., Lichtenberger F., Shapiro J., Russell K. C.: Tetrahedron Lett. 2000, 41, 6955. <https://doi.org/10.1016/S0040-4039(00)01181-3>
47. Alabugin I. V., Manoharan M., Kovalenko S. V.: Org. Lett. 2002, 4, 1119. <https://doi.org/10.1021/ol0255054>
48a. Kaneko T., Takahashi M., Hirama M.: Tetrahedron Lett. 1999, 40, 2015. <https://doi.org/10.1016/S0040-4039(99)00105-7>
48b. Thoen K. K., Thoen J. C., Uckun F. M.: Tetrahedron Lett. 2000, 41, 4019. <https://doi.org/10.1016/S0040-4039(00)00575-X>
49. Koseki S., Fujimura Y., Hirama M.: J. Phys. Chem. A 1999, 103, 7672. <https://doi.org/10.1021/jp991135y>
50. Jones G. B., Warner P. M.: J. Am. Chem. Soc. 2001, 123, 2134. <https://doi.org/10.1021/ja0033032>
51. Kim C.-S., Russell K. C.: J. Org. Chem. 1998, 63, 8229. <https://doi.org/10.1021/jo980879p>
52. Kim C.-S., Russell K. C.: Tetrahedron Lett. 1999, 40, 3835. <https://doi.org/10.1016/S0040-4039(99)00634-6>
53. Kim C.-S., Dietz C., Russell K. C.: Chem. Eur. J. 2000, 6, 1555. <https://doi.org/10.1002/(SICI)1521-3765(20000502)6:9<1555::AID-CHEM1555>3.3.CO;2-D>
54. Choy N., Russell K. C.: Heterocycles 1999, 51, 13.
55. David W. M., Kerwin S. M.: J. Am. Chem. Soc. 1997, 119, 1464. <https://doi.org/10.1021/ja962328r>
56. Hoffner J., Schottelius M. J., Feichtinger D., Chen P.: J. Am. Chem. Soc. 1998, 120, 376. <https://doi.org/10.1021/ja9730223>
57. Cramer C. J.: J. Am. Chem. Soc. 1998, 120, 6261. <https://doi.org/10.1021/ja9806579>