Synthesis of aromatic triynes as precursors to helicene derivatives

Collection of Czechoslovak Chemical Communications

Volumn 65, Issue 4, 2000, Pages 577-609

  Stará̈, Irena G ^a   Kollárovič, Adrian ^a   Teplý, Filip ^a   Starý, Ivo ^a   Šaman, David ^a   Fiedler, Pavel ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Acetylenes; Alkynes; Arenes; Cross coupling reactions; Cyclotrimerizations; Ethers; Helicenes; Sonogashira reaction; Triynes

Indexed keywords

EID: 0034344098     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20000577     Document Type: Article

References (68)

1. a) Whitesell J. K.: Chem. Rev. 1989, 89, 1581;
2. b) Červinka O.: Chem. Listy 1999, 93, 294.
3. a) Brunner H., Zettlmeier W.: Enantioselective Catalysis with Transition Metal Compounds. VCH, Weinheim 1993;
4. b) Jacobsen E. J., Pfaltz A., Yamamoto H. (Eds): Comprehensive Asymmetric Catalysis. Springer, Berlin 1999.
5. For reviews, see: a) Osuga H., Suzuki H. J.: Synth. Org. Chem., Jpn. 1994, 52, 1020;
6. b) Oremek G., Seiffert U., Janecka A.: Chem.-Ztg. 1987, 111, 69;
7. c) Vögtle F.: Fascinating Molecules in Organic Chemistry, p. 156. Wiley, New York 1992;
8. d) Meurer K. P., Vögtle F.: Top. Curr. Chem. 1985, 127, 1;
9. e) Laarhoven W. H., Prinsen W. J. C.: Top. Curr. Chem. 1984, 125, 63;
10. f) Martin K. H.: Angew. Chem. 1974, 86, 727;
11. g) Wynberg H.: Acc. Chem. Res. 1970, 4, 65.
12. a) Liu L., Katz T. J.: Tetrahedron Lett. 1990, 31, 3983;
13. b) Willmore N. D., Liu L. B., Katz T. J.: Angew. Chem., Int. Ed. Engl. 1992, 31, 1093.
14. a) Willmore N. D., Hoic D. A., Katz T. J.: J. Org. Chem. 1994, 59, 1889;
15. b) Shi S., Katz T. J., Yang B. V., Liu I.: J. Org. Chem. 1995, 60, 1285;
16. c) Dai Y. J., Katz T. J., Nichols D. A.: Angew. Chem., Int. Ed. Engl. 1996, 35, 2109;
17. d) Dai Y. J., Katz T. J.: J. Org. Chem. 1997, 62, 1274;
18. e) Katz T. J., Liu L. B., Willmore N. D., Fox J. M., Rheingold A. L., Shi S. H., Nuckolls C., Rickman B. H.: J. Am. Chem. Soc. 1997, 119, 10054;
19. f) Nuckolls C., Katz T. J.: J. Am. Chem. Soc. 1998, 120, 9541;
20. g) Fox J. M., Goldberg N. R., Katz T. J.: J. Org. Chem. 1998, 63, 7456;
21. h) Nuckolls C, Katz T. J., Katz G., Collings P. J., Castellanos L.: J. Am. Chem. Soc. 1999, 121, 79;
22. i) Fox J. M., Katz T. J.: J. Org. Chem. 1999, 64, 302;
23. j) Dreher S. D., Weix D. J., Katz T. J.: J. Org. Chem. 1999, 64, 3671;
24. k) Fox J. M., Katz T. J., Van Elshocht S., Verbiest T., Kauranen M., Persoons A., Thongpanchang T., Krauss T., Brus L.: J. Am. Chem. Soc. 1999, 121, 3453;
25. I) Dreher S. D., Paruch K., Katz T. J.: J. Org. Chem. 2000, 65, 806;
26. m) Dreher S. D., Katz T. J., Lain K. C., Rheingold A. L.: J. Org. Chem. 2000, 65, 815.
27. a) Tanaka K., Suzuki H., Osuga H.: Tetrahedron Lett. 1997, 38, 457;
28. b) Tanaka K., Suzuki LL, Osuga IL: J. Org. Chem. 1997, 62, 4465;
29. c) Dreher S. D.r Weix D. J., Katz T. J.: J. Org. Chem. 1999, 64, 3671.
30. a) Stará I. G., Starý I., Tichý M., Závada J., Hanuš V.: J. Am. Chem. Soc. 1994, 116, 5084;
31. b) Dore A., Fabbri D., Gladiali S., Valle G.: Tetrahedron: Asymmetry 1995, 6, 779;
32. c) Larsen J., Bcchgaard K.: J. Org. Chem. 1996, 61, 1151;
33. d) Pischel L, Grimme S., Kotila S., Nieger M., Vögtle F'.: Tetrahedron: Asyminetty 1996, 7, 109;
34. e) Cossu S., De Lucchi O., Fabbri D., Valle G., Painter G. F., Smith A. J.: Tetrahedron 1997, 53, 6073;
35. f) Minuti L., Taticchi A., Marrocchi A., Gacsbaitz E.: Tetrahedron 1997, 53, 6873;
36. g) Tanaka K., Suzuki H., Osuga H.: Tetrahedron Lett. 1997, 38, 457;
37. h) Tanaka K., Suzuki H., Osuga H.: J. Org. Chem. 1997, 62, 4465;
38. i) Minuti L., Taticchi A., Marrocchi A.: Synth. Commun. 1998, 28, 2181;
39. j) Dubois F., Gingras M.: Tetrahedron Lett. 1998, 39, 5039;
40. k) Gingras M., Dubois F.: Tetrahedron Lett. 1999, 40, 1309;
41. l) Carreno M. C, Hernández-Sánchez R., Mahugo J., Urbano A.: J. Org. Chem. 1999, 64, 1387.
42. a) Stará I. G., Starý L, Kollárovič A., Teplý F., Šaman D., Tichý M.: Chimia 1997, 51, 378;
43. b) Stará I. G., Stary I, Kollárovič A., Teplý F., Saman D., Tichý M.: J. Org. Chem. 1998, 63. 4046;
44. c) Stará I. G., Starý I., Kollárovič A., Teplý F., Vyskočil Š., Šaman D.: Tetrahedron Lett. 1999, 40, 1993.
45. 4 (Scheme 2). Dibromide 3 was routinely prepared from diol 2 on treatment with phosphorus tribromide (Scheme 2).
46. a) Thorand S., Krause N.: J. Org. Chem. 1998, 63, 8551;
47. b) Stará I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Fiedler P.: Collect. Czech. Chem. Commun. 1999, 64, 649.
48. Stará I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Fiedler P.: Tetrahedron 1998, 54, 11209.
49. a) Campbell I. D., Eglinton G., Raphael R. A.: J. Chem. Soc. B 1968, 338;
50. b) Staah H. A., Graf F.: Chem. Ber. 1970, 103, 1107.
51. 15.
52. a) Bunnett J. F.: Acc. Chem. Res. 1972, 5, 129;
53. b) Bělohradský M., Holý P., Závada J.: J. Chem. Soc., Perkin Trans. 2 1995, 1853.
54. Note, the direct base-mediated alkylation of diol 2 with (3-bromoprop-1-yn-1-yl)-trimethylsilane to produce 10 totally failed providing only the bissilylated diol 15.
55. a) Ozaki S., Matsushita H., Ohmori H.: J. Chem. Soc., Perkin Trans. 1 1993, 2339;
56. b) Oppolzer W., Ruiz-Montes J.: Helv. Chim. Acta 1993, 76, 1266;
57. c) Masquelin T., Obrecht D.: Synthesis 1995, 276;
58. d) Ince J., Ross T. M., Shipman M., Slawin A. M. Z., Ennis D. S.: Tetrahedron 1996, 52, 7037.
59. 19 (Scheme 4).
60. Henry J. R., Marcin L. R., McIntosh M., Scola P. M., Harris G. D., Jr., Weinreb S. M.: Tetrahedron Lett. 1989, 30, 5709.
61. Oppolzer W., Stammen B.: Tetrahedron 1997, 53, 3577.
62. Marshall J. A. in: Comprehensive Organic Synthesis (B. M. Trost, I. Fleming and L. A. Paquetre, Eds), Vol. 3, Chap. 3.11, p. 975. Pergamon Press, Oxford 1991.
63. a) Doetz K. H., Popall M.: Tetrahedron 1985, 41, 5797;
64. b) Brillon D.: Synth. Commun. 1986, 291;
65. c) Doetz K. H., Popall M., Mueller G.: J. Organomet. Chem. 1987, 334, 57;
66. d) Curran D. P., Kim D., Ziegler C.: Tetrahedron 1991, 47, 6189;
67. e) Llerena D., Buisine O., Aubert C., Malacria M.: Tetrahedron 1998, 54, 9373.
68. Atkinson R. S., Grimshire M. J.: J. Chem. Soc., Perkin Trans. 1 1986, 1215.