An efficient formal total synthesis of (±)-stypoldione via photochemically triggered biomimetic cyclizations of terpenoid polyalkenes

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 987-990

  Xing, Xuechao ^a   Demuth, Martin ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

( ) stypoldione synthesis; Biomimetic radical cyclization; Electron transfer; Photochemistry; Radical cation

Indexed keywords

ANTINEOPLASTIC AGENT; MARINE TOXIN; STYPOLDIONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; ELECTRON TRANSPORT; PHOTOCHEMISTRY; SYNTHESIS;

EID: 0032978789     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3110     Document Type: Article

References (60)

1. a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890;
2. b) Stork, G.; Burgstaler, A. W. J. Am. Chem, Soc. 1955, 77, 5068.
3. Simonson, J.; Ross, W. C. J., Eds., The Terpenes, Cambridge University Press: Cambridge, Vols. 1-5, 1947-1961.
4. For early reviews on cationic-type polyalkene cyclization, see: a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1;
5. b) Johnson, W. S. Bioorg. Chem. 1976, 5, 51;
6. c) Harding, K. E. Bioorg. Chem. 1973, 2, 248;
7. d) van Tamelen, E. E. Acc. Chem. Res. 1975, 8, 152.
8. For recent reviews on this theme, see: a) Johnson, W. S. Tetrahedron 1991, 47, xi-xxiv;
9. b) Sutherland, J. K. In Comprehensive Organic Synthesis, Vol. 3, p. 341, Trost, B. M.; Fleming, I., Eds., Pergamon: Oxford, 1991.
10. For recent papers in this area, see: a) Corey, E. J.; Lee, J. J. Am. Chem. Soc. 1993, 115, 8873;
11. b) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149;
12. c) Corey, E. J.; Wood, H. B. J. Am. Chem. Soc. 1996, 118, 11982;
13. d) Corey, E. J.; Lin, S. J. Am. Chem. Soc. 1996, 118, 8765;
14. e) Corey, E. J.; Luo, G.; Lin, L. S. J. Am. Chem. Soc. 1997, 119, 9927;
15. f) Corey, E. J.; Roberts, B. E. Tetrahedron Lett. 1997, 38, 8921;
16. g) Corey, E. J.; Staas, D. D. J. Am. Chem. Soc. 1998, 120, 3526.
17. a) Breslow, R.; Barrett, E.; Mohacsi, E. Tetrahedron Lett. 1962, 1207;
18. b) Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 1837.
19. a) Julia, M. Acc. Chem. Res. 1968, 1, 111;
20. b) Lallemand, J. Y.; Julia, M.; Mansuy, D. Tetrahedron Lett. 1973, 4461.
21. a) Curran, D. P. In Comprehensive Organic Synthesis, Vol. 4, p. 779, Trost, B. M.; Fleming, I., Eds., Pergamon: Oxford, 1991;
22. b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
23. a) Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2413, 2417;
24. b) Pattenden, G.; Smithies, A. J.; Tapolczay, D.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1, 1996, 7;
25. c) Begley, M. J.; Pattenden, G.; Smithies, A. J.; Tapolczay, D.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1, 1996, 21;
26. d) Batsanov, A.; Chen, L.; Gill, G. B.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1, 1996, 45;
27. e) Pattenden, G.; Wiedenau, P. Tetrahedron Lett. 1997, 38, 3647;
28. f) Handa, S.; Pattenden, G. Contemp. Org. Synth. 1997, 4, 196.
29. Caspi, E. Acc. Chem. Res. 1980, 13, 97; Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
30. Caspi, E. Acc. Chem. Res. 1980, 13, 97; Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
31. a) Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Krüger, C.; Roth, H. D., Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358;
32. b) Warzecha, K.-D.; Xing, X.; Demuth, M. Helv. Chim. Acta 1995, 78, 2065;
33. c) Warzecha, K.-D.; Xing, X.; Demuth, M. Pure Appl. Chem. 1997, 69 (1), 109;
34. d) Heinemann, C.; Warzecha, K.-D.; Xing, X.; Demuth, M. Indian J. Chem. 1997, 36 A&B, 494.
35. a) Xing, X.; Ph.D. Thesis, Max-Planck-Institut für Strahlenchemie/University of Essen, 1997;
36. b) Xing, X.; Demuth, M. EPA Newsletter, 1998, 64, 101;
37. c) Heinemann, C.; Xing, X.; Warzecha, K.-D.; Ritterskamp, P.; Demuth, M. Pure Appl. Chem. in press;
38. d) Heinemann, C.; Demuth, M. J. Am. Chem. Soc. 1999, in press.
39. a) Gerwick, W. H.; Fenical, W.; Fritsh, N.; Clardy, J. Tetrahedron Lett. 1979, 145;
40. b) Gerwick, W. H.; Fenical, W. J. Org. Chem. 1981, 46, 22.
41. a) White, S. J.; Jacobs, R. S. Mol. Pharmacol. 1983, 24, 500;
42. b) O'Brien, E.; Asai, T. D. J.; Jacobs, R. S.; Wilson, L. Mol. Pharmacol. 1989, 35, 635.
43. a) Begley, M. J.; Fish, P. V.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1, 1990, 2263;
44. b) Antus, S.; Bartz-Gacs, E.; Snatzke, G.; Vas, J. Tetrahedron 1986, 42, 5637;
45. c) Kaufman, T. S.; Sindelar, R. D. J. Heterocycl. Chem. 1989, 26, 879;
46. d) Corey, E. J.; Das, J. J. Am. Chem. Soc. 1982, 104, 5551;
47. e) McMurry, J. E.; Erion, M. D. ibid., 1985, 107, 2712;
48. f) Mori, K.; Komatsu, M. Liebigs Ann. Chem. 1988, 107;
49. g) Spanevello, R. A.; Gonzalez-Sierra, M.; Ruveda, E. A. Synth. Commun. 1986, 16, 749.
50. a) Mori, K.; Koga, Y. Bioorg. Med. Chem. Lett. 1992, 2, 391;
51. b) Mori, K.; Koga, Y. Liebigs Ann. 1995, 1755;
52. c) Falck, J. R.; Chandrasekhar, S.; Manna, S.; Chiu, C. S. J. Am. Chem. Soc. 1993, 115, 11606;
53. d) Abad, A.; Agullo, C.; Arno, M.; Cunat, A. C.; Meseguer, B.; Zaragoza, R. J. Synlett 1996, 913.
54. Geranylgeranyl acetate (5) and ethyl geranylgeranate were prepared according to the following refs.: a) van Tamelen, E. E.; Nadeau, R. G. Bioorg. Chem. 1982, 11, 197;
55. b) Klinge, S.; Demuth, M. Synlett 1993, 783.
56. a) Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13;
57. b) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
58. Bromide 10 was prepared according to the following refs.: a) Pearson, D. E.; Wysong, R. D.; Breder, C. V. J. Org. Chem. 1967, 32, 2358;
59. b) Raistrick, H.; Robinson, R.; White, D. E. Biochem. J. 1936, 30, 1303.
60. +) (88.4), 105 (100.0), 77 (15.7). * The chemical shifts are given in δ units (ppm). All coupling constants (J) are reported in Hz.