Collect. Czech. Chem. Commun. 2000, 65, 577-609
https://doi.org/10.1135/cccc20000577

Synthesis of Aromatic Triynes as Precursors to Helicene Derivatives

Irena G. Stará*, Adrian Kollárovič, Filip Teplý, Ivo Starý*, David Šaman and Pavel Fiedler

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

References

1a. Whitesell J. K.: Chem. Rev. 1989, 89, 1581. <https://doi.org/10.1021/cr00097a012>
1b. Červinka O.: Chem. Listy 1999, 93, 294.
2a. Brunner H., Zettlmeier W.: Enantioselective Catalysis with Transition Metal Compounds. VCH, Weinheim 1993.
2b. Jacobsen E. J., Pfaltz A., Yamamoto H. (Eds): Comprehensive Asymmetric Catalysis. Springer, Berlin 1999.
3a. Osuga H., Suzuki H. J.: Synth. Org. Chem., Jpn. 1994, 52, 1020. <https://doi.org/10.5059/yukigoseikyokaishi.52.1020>
3b. Oremek G., Seiffert U., Janecka A.: Chem.-Ztg. 1987, 111, 69.
3c. Vögtle F.: Fascinating Molecules in Organic Chemistry, p. 156. Wiley, New York 1992.
3d. Meurer K. P., Vögtle F.: Top. Curr. Chem. 1985, 127, 1. <https://doi.org/10.1007/BFb0049438>
3e. Laarhoven W. H., Prinsen W. J. C.: Top. Curr. Chem. 1984, 125, 63. <https://doi.org/10.1007/3-540-13569-3_3>
3f. Martin R. H.: Angew. Chem. 1974, 86, 727. <https://doi.org/10.1002/ange.19740862003>
3g. Wynberg H.: Acc. Chem. Res. 1970, 4, 65. <https://doi.org/10.1021/ar50038a004>
4a. Liu L., Katz T. J.: Tetrahedron Lett. 1990, 31, 3983. <https://doi.org/10.1016/S0040-4039(00)94478-2>
4b. Willmore N. D., Liu L. B., Katz T. J.: Angew. Chem., Int. Ed. Engl. 1992, 31, 1093. <https://doi.org/10.1002/anie.199210931>
5a. Willmore N. D., Hoic D. A., Katz T. J.: J. Org. Chem. 1994, 59, 1889. <https://doi.org/10.1021/jo00086a046>
5b. Shi S., Katz T. J., Yang B. V., Liu L.: J. Org. Chem. 1995, 60, 1285. <https://doi.org/10.1021/jo00110a036>
5c. Dai Y. J., Katz T. J., Nichols D. A.: Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. <https://doi.org/10.1002/anie.199621091>
5d. Dai Y. J., Katz T. J.: J. Org. Chem. 1997, 62, 1274. <https://doi.org/10.1021/jo9622284>
5e. 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. <https://doi.org/10.1021/ja9721327>
5f. Nuckolls C., Katz T. J.: J. Am. Chem. Soc. 1998, 120, 9541. <https://doi.org/10.1021/ja982025s>
5g. Fox J. M., Goldberg N. R., Katz T. J.: J. Org. Chem. 1998, 63, 7456. <https://doi.org/10.1021/jo981380y>
5h. Nuckolls C., Katz T. J., Katz G., Collings P. J., Castellanos L.: J. Am. Chem. Soc. 1999, 121, 79. <https://doi.org/10.1021/ja983248l>
5i. Fox J. M., Katz T. J.: J. Org. Chem. 1999, 64, 302. <https://doi.org/10.1021/jo9817570>
5j. Dreher S. D., Weix D. J., Katz T. J.: J. Org. Chem. 1999, 64, 3671. <https://doi.org/10.1021/jo990065o>
5k. 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. <https://doi.org/10.1021/ja983633a>
5l. Dreher S. D., Paruch K., Katz T. J.: J. Org. Chem. 2000, 65, 806. <https://doi.org/10.1021/jo9914972>
5m. Dreher S. D., Katz T. J., Lam K. C., Rheingold A. L.: J. Org. Chem. 2000, 65, 815. <https://doi.org/10.1021/jo991498u>
6a. Tanaka K., Suzuki H., Osuga H.: Tetrahedron Lett. 1997, 38, 457. <https://doi.org/10.1016/S0040-4039(96)02325-8>
6b. Tanaka K., Suzuki H., Osuga H.: J. Org. Chem. 1997, 62, 4465. <https://doi.org/10.1021/jo970272t>
6c. Dreher S. D., Weix D. J., Katz T. J.: J. Org. Chem. 1999, 64, 3671. <https://doi.org/10.1021/jo990065o>
7a. Stará I. G., Starý I., Tichý M., Závada J., Hanuš V.: J. Am. Chem. Soc. 1994, 116, 5084. <https://doi.org/10.1021/ja00091a009>
7b. Dore A., Fabbri D., Gladiali S., Valle G.: Tetrahedron: Asymmetry 1995, 6, 779. <https://doi.org/10.1016/0957-4166(95)00074-Y>
7c. Larsen J., Bechgaard K.: J. Org. Chem. 1996, 61, 1151. <https://doi.org/10.1021/jo951277y>
7d. Pischel I., Grimme S., Kotila S., Nieger M., Vögtle F.: Tetrahedron: Asymmetry 1996, 7, 109. <https://doi.org/10.1016/0957-4166(95)00427-0>
7e. Cossu S., De Lucchi O., Fabbri D., Valle G., Painter G. F., Smith A. J.: Tetrahedron 1997, 53, 6073. <https://doi.org/10.1016/S0040-4020(97)00268-8>
7f. Minuti L., Taticchi A., Marrocchi A., Gacsbaitz E.: Tetrahedron 1997, 53, 6873. <https://doi.org/10.1016/S0040-4020(97)00318-9>
7g. Tanaka K., Suzuki H., Osuga H.: Tetrahedron Lett. 1997, 38, 457. <https://doi.org/10.1016/S0040-4039(96)02325-8>
7h. Tanaka K., Suzuki H., Osuga H.: J. Org. Chem. 1997, 62, 4465. <https://doi.org/10.1021/jo970272t>
7i. Minuti L., Taticchi A., Marrocchi A.: Synth. Commun. 1998, 28, 2181. <https://doi.org/10.1080/00397919808007032>
7j. Dubois F., Gingras M.: Tetrahedron Lett. 1998, 39, 5039. <https://doi.org/10.1016/S0040-4039(98)00996-4>
7k. Gingras M., Dubois F.: Tetrahedron Lett. 1999, 40, 1309. <https://doi.org/10.1016/S0040-4039(98)02670-7>
7l. Carreno M. C., Hernández-Sánchez R., Mahugo J., Urbano A.: J. Org. Chem. 1999, 64, 1387. <https://doi.org/10.1021/jo981919s>
8a. Stará I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Tichý M.: Chimia 1997, 51, 378.
8b. Stará I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Tichý M.: J. Org. Chem. 1998, 63, 4046. <https://doi.org/10.1021/jo9801263>
8c. Stará I. G., Starý I., Kollárovič A., Teplý F., Vyskočil Š., Šaman D.: Tetrahedron Lett. 1999, 40, 1993. <https://doi.org/10.1016/S0040-4039(99)00099-4>
9. Diester 1 and diol 2 were easily prepared in one step from methyl 2-iodobenzoate10 or 2-iodobenzyl alcohol11, respectively, and dibromide 3 in two steps from 2-iodo- 4-methylbenzene11,12. In addition, diester 1 was reduced to diol 2 with Na[AlH2(OCH2CH2OCH3)2] leaving the triple bond untouched in contrast to LiAlH4 (Scheme 2). Dibromide 3 was routinely prepared from diol 2 on treatment with phosphorus tribromide (Scheme 2).
10a. Thorand S., Krause N.: J. Org. Chem. 1998, 63, 8551. <https://doi.org/10.1021/jo9808021>
10b. Stará I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Fiedler P.: Collect. Czech. Chem. Commun. 1999, 64, 649. <https://doi.org/10.1135/cccc19990649>
11. Stará I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Fiedler P.: Tetrahedron 1998, 54, 11209. <https://doi.org/10.1016/S0040-4020(98)00655-3>
12a. Campbell I. D., Eglinton G., Raphael R. A.: J. Chem. Soc. B 1968, 338. <https://doi.org/10.1039/j29680000338>
12b. Staab H. A., Graf F.: Chem. Ber. 1970, 103, 1107. <https://doi.org/10.1002/cber.19701030415>
13. For structure assignment, compound 11 was hydrogenated over palladium on charcoal to produce the 1,3-dihydro-2-benzofuran derivatives 12 and 13.
14. Triyne 9 was accompanied by the minor rearranged dibromide 14 being produced by a “halogen dance” under basic conditions15.
15a. Bunnett J. F.: Acc. Chem. Res. 1972, 5, 129. <https://doi.org/10.1021/ar50052a004>
15b. Bělohradský M., Holý P., Závada J.: J. Chem. Soc., Perkin Trans. 2 1995, 1853. <https://doi.org/10.1039/p29950001853>
16. 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.
17a. Ozaki S., Matsushita H., Ohmori H.: J. Chem. Soc., Perkin Trans. 1 1993, 2339. <https://doi.org/10.1039/p19930002339>
17b. Oppolzer W., Ruiz-Montes J.: Helv. Chim. Acta 1993, 76, 1266. <https://doi.org/10.1002/hlca.19930760313>
17c. Masquelin T., Obrecht D.: Synthesis 1995, 276. <https://doi.org/10.1055/s-1995-3893>
17d. Ince J., Ross T. M., Shipman M., Slawin A. M. Z., Ennis D. S.: Tetrahedron 1996, 52, 7037. <https://doi.org/10.1016/0040-4020(96)00308-0>
18. Sulfonamides 21 (ref.17) and 22 are readily available from prop-2-yn-1-ol and but-2-yn-1-ol, respectively, exploiting the general protocol of Weinreb19 (Scheme 4).
19. Henry J. R., Marcin L. R., McIntosh M., Scola P. M., Harris G. D., Jr., Weinreb S. M.: Tetrahedron Lett. 1989, 30, 5709. <https://doi.org/10.1016/S0040-4039(00)76177-6>
20. Oppolzer W., Stammen B.: Tetrahedron 1997, 53, 3577. <https://doi.org/10.1016/S0040-4020(97)00077-X>
21. Marshall J. A. in: Comprehensive Organic Synthesis (B. M. Trost, I. Fleming and L. A. Paquette, Eds), Vol. 3, Chap. 3.11, p. 975. Pergamon Press, Oxford 1991.
22a. Doetz K. H., Popall M.: Tetrahedron 1985, 41, 5797. <https://doi.org/10.1016/S0040-4020(01)91419-X>
22b. Brillon D.: Synth. Commun. 1986, 291. <https://doi.org/10.1080/00397918608076311>
22c. Doetz K. H., Popall M., Mueller G.: J. Organomet. Chem. 1987, 334, 57. <https://doi.org/10.1016/0022-328X(87)80038-4>
22d. Curran D. P., Kim D., Ziegler C.: Tetrahedron 1991, 47, 6189. <https://doi.org/10.1016/S0040-4020(01)86551-0>
22e. Llerena D., Buisine O., Aubert C., Malacria M.: Tetrahedron 1998, 54, 9373. <https://doi.org/10.1016/S0040-4020(98)00567-5>
23. Atkinson R. S., Grimshire M. J.: J. Chem. Soc., Perkin Trans. 1 1986, 1215. <https://doi.org/10.1039/p19860001215>