Novel method for the synthesis of α- and β-halogenonaphthalenes by regioselective benzannulation of aryl(gem-dihalogenocyclopropyl)methanols: Application to the total synthesis of the lignan lactones, justicidin E and taiwanin C

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1996, Pages 2157-2165

  Tanabe, Yoo ^a   Seko, Shinzo ^b   Nishii, Yoshinori ^a   Yoshida, Taichi ^a   Utsumi, Naoka ^b   Suzukamo, Gohfu ^b  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748976541     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002157     Document Type: Article

References (67)

1. Part of this work appeared in a preliminary communication: S. Seko, Y. Tanabe and G. Suzukamo, Tetrahedron Lett., 1990, 31, 6883.
2. (a) H. N. C. Wong, M.-Y. Hon, C.-Y. Tse, Y.-C. Yip, J. Tanko and T. Hudlicky, Chem. Rev., 1989, 89, 165;
3. (b) U.-H. Reißig, Top. Curr. Chem., 1988, 144, 73.
4. (a) D. Cartwrite, P. Langcake, R. J. Pryce, D. P. Leworthy and J. P. Ride, Nature, 1977, 267, 511;
5. (b) G. Holan, D. F. O'Keefe, C. Vergona and R. Walser, Nature, 1978, 272, 734;
6. (c) Y. Kurahashi, S. Kagabu, N. Matsumoto, T. Yamada, K. Wada and T. Kondo, Jap P 54 349/1988 (Chem. Abstr., 1988, 109, 190038h).
7. (a) W. E. Paham and E. E. Schweizer, Organic Reactions, Wiley, New York, 1963, vol. 13, p. 55;
8. (b) C. M. Starks and C. Liotta, Phase Transfer Catalysis, Academic Press, New York, 1978, p. 224.
9. (a) D. Seyferth, H. Yamazaki and D. L. Alleston, J. Org. Chem., 1963, 28, 703;
10. (b) T. Ando, H. Yamanaka, F. Namigata and W. Funasaka, J. Am. Chem. Soc., 1967, 89, 5719;
11. (c) R. M. Blankenship, K. A. Burdett and J. S. Swenton, J. Am. Chem. Soc., 1974, 39, 2300;
12. (d) L. K. Sydnes and L. Skattebøl, Tetrahedron Lett., 1974, 3703;
13. (e) T. Hirao, T. Masunaga, Y. Ohshiro and T. Agawa, J. Org. Chem., 1981, 46, 3745;
14. (f) A. Osuka, K. Takeuchi and H. Suzuki, Bull. Chem. Soc. Jpn., 1984, 57, 303;
15. (g) K. Miura, Y. Ichinose K. Fugami, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1989, 62, 143;
16. (h) T. Hirao, K. Hirano, T. Hasegawa, Y. Ohshiro and I. Ikeda, J. Org. Chem., 1993, 58, 6529;
17. (i) Y. Apeloig and M. Nakash, J. Am. Chem. Soc., 1994, 116, 10084.
18. T. Hiyama, M. Tsukanaka and H. Nozaki, J. Am. Chem. Soc., 1974, 96, 3713.
19. For recent study of transformation of gem-dihalogenocyclopropane (a) M. Mitani, Y. Kobayashi and K. Koyama, J. Chem. Soc., Perkin Trans. 1, 1995, 653;
20. (b) S. Kagabu, C. Ando and J. Ando, J. Chem. Soc., Perkin Trans. 1, 1996, 739;
21. (c) M. Mitani, Y. Kobayashi and K. Koyama, J. Chem. Soc., Perkin Trans. 1, 1995, 653;
22. (d) J. R. A. Dulayymi and M. S. Baird, Tetrahedron Lett., 1995, 36, 3393;
23. (e) A. R. A. Dulayymi, J. R. A. Dulayymi, M. S. Baird and L. Rajaram, Tetrahedron, 1995, 8371.
24. (a) K. H. Holm and L. Skattebøl, Tetrahedron Lett., 1977, 2347;
25. (b) K. H. Holm and L. Skattebøl, J. Am. Chem. Soc., 1977, 99, 5480;
26. (c) K. H. Holm, E. A. Mohamed and L. Skattebøl, Acta Chem. Scand., 1993, 47, 500.
27. (a) K. Kitatani, T. Hiyama and H. Nozaki, Bull. Chem. Soc. Jpn., 1977, 50, 1600;
28. (b) T. Harada, T. Katsuhira, K. Hattori and A. Oku, J. Org. Chem., 1993, 58, 2958;
29. (c) T. Harada, T. Katsuhira, K. Hattori and A. Oku, Tetrahedron, 1994, 50, 7987.
30. (a) Y. Tanabe, Y. Nishii and K. Wakimura, Chem. Lett., 1994, 1757;
31. (b) Y. Tanabe, K. Wakimura and Y. Nishii, Tetrahedron Lett., 1996, 37, 1837.
32. (a) Y. Nishii and Y. Tanabe, Tetrahedron Lett., 1995, 36, 8803;
33. (b) Y. Nishii, H. Matsumura, Y. Muroya, T. Tsuchiya and Y. Tanabe, Biosci. Biotech. Biochem., 1995, 59, 1355;
34. (c) Y. Tanabe, K. Wakimura, Y. Nishii and Y. Muroya, Synthesis, 1996, 388;
35. (d) Y. Nishii, K. Wakimura, T. Tsuchiya, S. Nakamura and Y. Tanabe, J. Chem. Soc., Perkin Trans. 1, 1996, 1243.
36. K. Wada and K. Munakata, Tetrahedron Lett., 1970, 2017.
37. Y.-T. Lin, T.-B. Lo, K. T. Wang and B. Weinstein, Tetrahedron Lett., 1967, 849.
38. Previous syntheses: (a) T. L. Holmes and R. Stevenson, J. Chem. Soc. C, 1971, 2091;
39. (b) T. L. Holmes and R. Stevenson, J. Org. Chem., 1971, 36, 3450;
40. (c) E. Block and R. Stevenson, J. Org. Chem., 1971, 36, 3450;
41. (d) B. J. Arnold, S. M. Mellows and P. G. Sammes, J. Chem. Soc., Perkin Trans. 1, 1973, 1266;
42. (e) Z. Horii, M. Tujiuchi, K. Kanai and T. Momose, Chem. Pharm. Bull., 25, 1977, 1803. For recent syntheses:
43. (f) T. Hattori, H. Tanaka, Y. Okaishi and S. Miyano, J. Chem. Soc., Perkin Trans. 1, 1995, 235;
44. (g) J. E. Cochran and A. Padwa, J. Org. Chem., 1995, 60, 3938;
45. (h) T. Ogiku, S. Yoshida, H. Ohmizu and T. Iwasaki, J. Org. Chem., 1995, 60, 4585;
46. (i) K. Kobayashi, J. Tokimatsu, K. Maeda, O. Morikawa and H. Konishi, J. Chem. Soc., Perkin Trans. 1, 1995, 3013.
47. (a) Y. Tanabe, G. Suzukamo, Y. Komuro, N. Imanishi, S. Morooka, M. Enomoto, A. Kojima, Y. Sanemitsu and M. Mizutani, Tetrahedron Lett., 1991, 32, 379;
48. (b) Y. Tanabe, Y. Kubota, Y. Sanemitsu, N. Itaya and G. Suzukamo, Tetrahedron Lett., 1991, 32, 383;
49. (c) Y. Tanabe, H. Yamamoto, M. Murakami, K. Yanagi, Y. Kubota, H. Okumura, Y. Sanemitsu and G. Suzukamo, J. Chem. Soc., Perkin Trans. 1, 1995, 935;
50. (d) Y. Tanabe, H. Okumura, M. Nagaosa and M. Murakami, Bull. Chem. Soc. Jpn., 1995, 68, 1467.
51. (a) D. J. Hanahan, Ann. Rev. Biochem., 1986, 55, 483;
52. (b) M. N. Chang, Drugs of the Future, 1986, 11, 869;
53. (c) M. Shiraiwa, K. Fujita, H. Yoshiwara, S. Kobayashi and M. Ohno, J. Synth. Org. Chem. Jpn., 1987, 45, 369;
54. (d) M. Koltai and P. G. Braquet, Clinical Reviews in Allergy, 1994, 12, 361.
55. (a) F. T. DeWeese, D. E. Minter, J. T. Nosovitch and M. G. Rudel, Tetrahedron, 1986, 42, 4195;
56. (b) C. S-Rouvier, Tetrahedron, 1981, 37, 4195.
57. (a) S. Shuto, S. Ono, Y. Hase, N. Kamiyama, H. Takada, K. Yamashita and A. Matsuda, J. Org. Chem., 1996, 61, 915;
58. (b) A. S. Cieplak, J. Am. Chem. Soc., 1981, 103, 4540;
59. (c) A. S. Cieplak, B. D. Tait and C. R. Johnson, J. Am. Chem. Soc., 1989, 111, 8447.
60. T. Mukaiyama, M. Hayashi and K. Narasaka, Chem. Lett., 1973, 291.
61. M. Fetizon, M. Golfier and J.-M. Louis, J. Chem. Soc., Chem. Commun., 1969, 1102 and 1118.
62. (a) British Drug Houses Ltd., Neth. Appl. 6506881, 1965 (Chem. Abstr., 1966, 64, p. 17445e);
63. (b) I. A. D'yakonov and L. P. Denilkina, Zh. Obshch. Khim., 1964, 34, 38
64. (Chem. Abstr., 1964, 60, 15745c).
65. K. Kleveland, L. Skattebøl and L. K. Sydnes, Acta Chem. Scand., Ser. B, 1977, 31, 463.
66. D. Seyferth, J. M. Burlitch, R. J. Minasz, J. V.-P. Mui, H. D. Simmons, Jr., A. J. H. Treiber and S. R. Dowd, J. Am. Chem. Soc., 1965, 87, 4259.
67. K. R. Bedford, G. W. Burton, M. Dela, B. D. Peter and H. Suzuki, J. Chem. Soc., Perkin Trans. 2, 1974, 459.