Macrocyclic amides consisting of helical chiral 1,12- dimethylbenzo[c]phenanthrene-5,8-dicarboxylate

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9500-9509

  Okubo, Hitoshi ^a   Yamaguchi, Masahiko ^a   Kabuto, Chizuko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,12 DIMETHYLBENZO[C]PHENANTHRENE 5,8 DICARBOXYLIC ACID; ALDEHYDE; AMIDE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032509543     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981720f     Document Type: Article

References (42)

1. Reviews: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. Osuga, H.; Suzuki, H. J. Synth. Org. Chem., Jpn. 1994, 52, 1020. For some recent examples: Nakazaki, M.; Yamamoto, K.; Maeda, M. J. Org. Chem. 1981, 46, 1985. Sudhakar, A.; Katz, T. J. J. Am. Chem. Soc. 1986, 108, 179. Pereira, D. E.; Neelima, Leonard, N. J. Tetrahedron 1990, 46, 5895. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Also see references therein.
2. Reviews: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. Osuga, H.; Suzuki, H. J. Synth. Org. Chem., Jpn. 1994, 52, 1020. For some recent examples: Nakazaki, M.; Yamamoto, K.; Maeda, M. J. Org. Chem. 1981, 46, 1985. Sudhakar, A.; Katz, T. J. J. Am. Chem. Soc. 1986, 108, 179. Pereira, D. E.; Neelima, Leonard, N. J. Tetrahedron 1990, 46, 5895. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Also see references therein.
3. Reviews: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. Osuga, H.; Suzuki, H. J. Synth. Org. Chem., Jpn. 1994, 52, 1020. For some recent examples: Nakazaki, M.; Yamamoto, K.; Maeda, M. J. Org. Chem. 1981, 46, 1985. Sudhakar, A.; Katz, T. J. J. Am. Chem. Soc. 1986, 108, 179. Pereira, D. E.; Neelima, Leonard, N. J. Tetrahedron 1990, 46, 5895. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Also see references therein.
4. Reviews: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. Osuga, H.; Suzuki, H. J. Synth. Org. Chem., Jpn. 1994, 52, 1020. For some recent examples: Nakazaki, M.; Yamamoto, K.; Maeda, M. J. Org. Chem. 1981, 46, 1985. Sudhakar, A.; Katz, T. J. J. Am. Chem. Soc. 1986, 108, 179. Pereira, D. E.; Neelima, Leonard, N. J. Tetrahedron 1990, 46, 5895. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Also see references therein.
5. Reviews: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. Osuga, H.; Suzuki, H. J. Synth. Org. Chem., Jpn. 1994, 52, 1020. For some recent examples: Nakazaki, M.; Yamamoto, K.; Maeda, M. J. Org. Chem. 1981, 46, 1985. Sudhakar, A.; Katz, T. J. J. Am. Chem. Soc. 1986, 108, 179. Pereira, D. E.; Neelima, Leonard, N. J. Tetrahedron 1990, 46, 5895. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Also see references therein.
6. Reviews: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. Osuga, H.; Suzuki, H. J. Synth. Org. Chem., Jpn. 1994, 52, 1020. For some recent examples: Nakazaki, M.; Yamamoto, K.; Maeda, M. J. Org. Chem. 1981, 46, 1985. Sudhakar, A.; Katz, T. J. J. Am. Chem. Soc. 1986, 108, 179. Pereira, D. E.; Neelima, Leonard, N. J. Tetrahedron 1990, 46, 5895. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Also see references therein.
7. Nakazaki, M.; Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y. J. Chem. Soc., Chem. Commun. 1983, 787. Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans I 1990, 271.
8. Nakazaki, M.; Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y. J. Chem. Soc., Chem. Commun. 1983, 787. Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans I 1990, 271.
9. Hassine, B. B.; Gorsane, M.; Pecher, J.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 597. Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557.
10. Hassine, B. B.; Gorsane, M.; Pecher, J.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 597. Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557.
11. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Lovinger, A. J.; Nuckolls, C.; Katsz, T. J. J. Am. Chem. Soc. 1998, 120, 264. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Also see references therein.
12. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Lovinger, A. J.; Nuckolls, C.; Katsz, T. J. J. Am. Chem. Soc. 1998, 120, 264. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Also see references therein.
13. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Lovinger, A. J.; Nuckolls, C.; Katsz, T. J. J. Am. Chem. Soc. 1998, 120, 264. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Also see references therein.
14. Newman, M. S.; Wolf, M. J. Am. Chem. Soc. 1952, 74, 3225. Newman, M. S.; Wise, R. M. J. Am. Chem. Soc. 1956, 78, 450.
15. Newman, M. S.; Wolf, M. J. Am. Chem. Soc. 1952, 74, 3225. Newman, M. S.; Wise, R. M. J. Am. Chem. Soc. 1956, 78, 450.
16. Preliminary results. Yamaguchi, M.; Okubo, H.; Hirama, M. J. Chem. Soc., Chem. Commun. 1996, 1771.
17. Chemistry of optically active hexahelicene-7, 7′-dicarboxylate. Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. I 1981, 350. Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336.
18. Chemistry of optically active hexahelicene-7, 7′-dicarboxylate. Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. I 1981, 350. Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336.
19. Cheung, J.; Field, L. D.; Hambley, T. W.; Sternhell, S. J. Org. Chem. 1997, 62, 62.
20. Oda, M.; Yamamuro, A.; Watabe, T. Chem. Lett. 1979, 1427.
21. Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc. 1993, 115, 7547. Harada, N.; Soutome, T.; Murai, S.; Uda, H. Tetrahedron: Asymmetry 1993, 4, 1755.
22. Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc. 1993, 115, 7547. Harada, N.; Soutome, T.; Murai, S.; Uda, H. Tetrahedron: Asymmetry 1993, 4, 1755.
23. Kano, K.; Negi, S.; Takaoka, R.; Kamo, H.; Kitae, T.; Yamaguchi, M.; Okubo, H.; Hirama, M. Chem. Lett. 1997, 715. Kano, K.; Negi, S.; Kamo, H.; Kitae, T.; Yamaguchi, M.; Okubo, H.; Hirama, M. Chem. Lett. 1998, 151.
24. Kano, K.; Negi, S.; Takaoka, R.; Kamo, H.; Kitae, T.; Yamaguchi, M.; Okubo, H.; Hirama, M. Chem. Lett. 1997, 715. Kano, K.; Negi, S.; Kamo, H.; Kitae, T.; Yamaguchi, M.; Okubo, H.; Hirama, M. Chem. Lett. 1998, 151.
25. Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. Ottens-Hildebrandt, S.; Nieger, M.; Rissannen, K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1995, 777. Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930.
26. Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. Ottens-Hildebrandt, S.; Nieger, M.; Rissannen, K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1995, 777. Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930.
27. Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. Ottens-Hildebrandt, S.; Nieger, M.; Rissannen, K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1995, 777. Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930.
28. Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. Ottens-Hildebrandt, S.; Nieger, M.; Rissannen, K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1995, 777. Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930.
29. Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. Ottens-Hildebrandt, S.; Nieger, M.; Rissannen, K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1995, 777. Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930.
30. Horman, I.; Dreux, B. Helv. Chim. Acta 1984, 67, 754.
31. Bellamy, L. J. The Infra-red Spectra of Complex Molecules; Chapman and Hall: London, 1975; Chapter 12, p 231.
32. Itai, A.; Toriumi, Y.; Tomioka, N.; Kagechika, H.; Azumaya, I.; Shudo, K. Tetrahedron Lett. 1989, 30, 6177. Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10649.
33. Itai, A.; Toriumi, Y.; Tomioka, N.; Kagechika, H.; Azumaya, I.; Shudo, K. Tetrahedron Lett. 1989, 30, 6177. Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10649.
34. The calculation was conducted using Amber* (McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7743) contained in the MacroModel Ver 6.0. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulsfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
35. The calculation was conducted using Amber* (McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7743) contained in the MacroModel Ver 6.0. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulsfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
36. For reviews: Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
37. For reviews: Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
38. Feng, F.; Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc., 1998, 120, 10166.
39. Pickard, R. H.; Kenyon, J. J. Chem. Soc. 1914, 1115.
40. Capillon, J.; Guétté, J.-P. Tetrahedron. 1979, 35, 1817.
41. Niwa, S.; Soai, K. J. Chem. Soc., Perkin. Trans. I 1991, 2717.
42. Oguni, N.; Omi, T.; Yamamoto, Y.; Nakamura, A. Chem. Lett. 1983, 841.