Studies on the Synthesis of Phytochrome and Related Tetrapyrroles. Dihydropyrromethenones by Photochemical Rearrangement of N-Pyrrolo Enamides

Journal of Organic Chemistry

Volumn 62, Issue 9, 1997, Pages 2894-2906

  Jacobi, Peter A ^a   Buddhu, Subhas C ^a   Fry, Douglas ^a   Rajeswari, S ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001216690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970288j     Document Type: Article

References (67)

1. Moses, P. B.; Chua, N.-H. Sci. Am. 1988, 258, 88.
2. Phytochrome and Photoregulation in Plants, Furuya, M., Ed.; Academic Press: New York, 1987.
3. Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer-Verlag: Vienna-New York, 1989.
4. For a review on biliproteins see: Scheer, H. Angew. Chem. 1981, 93, 230; Angew. Chem., Int. Ed. Engl. 1981, 20, 241.
5. For a review on biliproteins see: Scheer, H. Angew. Chem. 1981, 93, 230; Angew. Chem., Int. Ed. Engl. 1981, 20, 241.
6. For a review of linear tetrapyrrole chemistry see: Tetrahedron 1983, 39, 1839, Symposia-In-Print, Bonnett, R., Ed.
7. For reviews on phytochrome-mediated responses in plants, see: (a) Statter, R. L.; Galston, A. W. in Chemistry and Biochemistry of Plant Pigments; Goodwin, T. W., Ed.; Academic Press: New York, 1976; Vol. 1, p 680. (b) Rüdiger, W.; Thümmler, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1216. (c) Rüdiger, W. Photochem. Photobiol. 1992, 56, 803. (d) Song, P.-S. The Spectrum (Bowling Green State University) 1994, 7, 1 (Issue 2).
8. For reviews on phytochrome-mediated responses in plants, see: (a) Statter, R. L.; Galston, A. W. in Chemistry and Biochemistry of Plant Pigments; Goodwin, T. W., Ed.; Academic Press: New York, 1976; Vol. 1, p 680. (b) Rüdiger, W.; Thümmler, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1216. (c) Rüdiger, W. Photochem. Photobiol. 1992, 56, 803. (d) Song, P.-S. The Spectrum (Bowling Green State University) 1994, 7, 1 (Issue 2).
9. For reviews on phytochrome-mediated responses in plants, see: (a) Statter, R. L.; Galston, A. W. in Chemistry and Biochemistry of Plant Pigments; Goodwin, T. W., Ed.; Academic Press: New York, 1976; Vol. 1, p 680. (b) Rüdiger, W.; Thümmler, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1216. (c) Rüdiger, W. Photochem. Photobiol. 1992, 56, 803. (d) Song, P.-S. The Spectrum (Bowling Green State University) 1994, 7, 1 (Issue 2).
10. For reviews on phytochrome-mediated responses in plants, see: (a) Statter, R. L.; Galston, A. W. in Chemistry and Biochemistry of Plant Pigments; Goodwin, T. W., Ed.; Academic Press: New York, 1976; Vol. 1, p 680. (b) Rüdiger, W.; Thümmler, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1216. (c) Rüdiger, W. Photochem. Photobiol. 1992, 56, 803. (d) Song, P.-S. The Spectrum (Bowling Green State University) 1994, 7, 1 (Issue 2).
11. For reviews on phytochrome biochemistry and chromophore chemistry, see: (a) Terry, M. J.; Wahleithner, J. A.; Lagarias, J. C. Arch. Biochem. Biophys. 1993, 306, 1. (b) Pratt, L. H. Photochem. Photobiol. 1978, 27, 81. (c) Kendrick, R. E.; Spruit, C. J. P. Photoche. Photobiol. 1977, 26, 201.
12. For reviews on phytochrome biochemistry and chromophore chemistry, see: (a) Terry, M. J.; Wahleithner, J. A.; Lagarias, J. C. Arch. Biochem. Biophys. 1993, 306, 1. (b) Pratt, L. H. Photochem. Photobiol. 1978, 27, 81. (c) Kendrick, R. E.; Spruit, C. J. P. Photoche. Photobiol. 1977, 26, 201.
13. For reviews on phytochrome biochemistry and chromophore chemistry, see: (a) Terry, M. J.; Wahleithner, J. A.; Lagarias, J. C. Arch. Biochem. Biophys. 1993, 306, 1. (b) Pratt, L. H. Photochem. Photobiol. 1978, 27, 81. (c) Kendrick, R. E.; Spruit, C. J. P. Photoche. Photobiol. 1977, 26, 201.
14. Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein.
15. (a) Glazer, A. N. in The Biochemistry of Plants; Hatch, M. D.; Boardman, N. K., Eds.; Academic Press: New York, 1981; Vol. 8, p 51.
16. (b) Carra, P. O.; O hEocha, C., in ref 6a, p 328.
17. (c) Schoenleber, R. W.; Leung, S.-L.; Lundell, D. J.; Glazer, A. N.; Rapoport, H. J. Am. Chem. Soc. 1983, 105, 4072.
18. Rüdiger, W. Struct. Bonding 1980, 40, 101. See also refs 4 and 6.
19. (a) Lagarias, J. C.; Rapoport, H. J. Am. Chem. Soc, 1980, 102, 4821.
20. (b) Micura, R.; Grubmayr, K. Bioorg. Med. Chem. Lett. 1994, 4, 2517.
21. (a) Thümmler, F.; Rüdiger, W. Tetrahedron 1983, 39, 1943.
22. (b) Rüdiger, W.; Thümmler, F.; Cmiel, E.; Schneider, S. Proc. Natl. Acad. Sci. 1983, 80, 6244.
23. (c) Farrens, D. L.; Holt, R. E.; Rospendowski, B. N.; Song, P.-S.; Cotton, T. M. J. Am. Chem. Soc. 1989, 111, 9162.
24. (d) Fodor, S. P. A.; Lagarias, J. C.; Mathies, R. A. Biochemistry 1990, 29, 11141.
25. (e) Fodor, S. P. A.; Lagarias, J. C.; Mathies, R. A. Photochem. Photobiol. 1988, 48, 129.
26. (a) Grombein, S.; Rüdiger, W.; Zimmermann, H. Hoppe-Seyler's Z. Physiol. Chem. 1975, 356, 1709.
27. (b) Klein, G.; Grombein, S.; Rüdiger, W. Ibid. 1977, 358, 1077.
28. Rüdiger, W.; Brandlmeier, T.; Blos, I.; Gossauer, A.; Welle, J.-P. Z. Naturforsch., Teil C 1980, 35, 763.
29. (a) Scheer, H.; Krauss, C. Photochem. Photobiol. 1977, 25, 311.
30. (b) Scheer, H.; Linsenmeier, U.; Krauss, C. Hoppe-Seyler's Z. Physiol. Chem. 1977, 358, 185.
31. (c) Krauss, C.; Bubenzer, C.; Scheer, H. Photochem. Photobiol. 1979, 29, 473.
32. See, for example: (a) Smith, K. M.; Kishore, D. Tetrahedron 1983, 39, 1841. (b) Cavaleiro, J. A. S.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1973, 2149. (c) Barnett, G. H.; Hudson, M. F.; McCombie, S. W.; Smith, K. M. J. Chem. Soc., Perkin Trans, 1 1973, 691. (d) Smith, K. M.; Sharkus, L. C.; Dallas, J. L. Biochem. Biophys. Res. Commun. 1980, 97, 1370. (e) Bonnett, R.; McDonagh, A. F. J. Chem. Soc., Perkin Trans. 1 1973, 881.
33. See, for example: (a) Smith, K. M.; Kishore, D. Tetrahedron 1983, 39, 1841. (b) Cavaleiro, J. A. S.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1973, 2149. (c) Barnett, G. H.; Hudson, M. F.; McCombie, S. W.; Smith, K. M. J. Chem. Soc., Perkin Trans, 1 1973, 691. (d) Smith, K. M.; Sharkus, L. C.; Dallas, J. L. Biochem. Biophys. Res. Commun. 1980, 97, 1370. (e) Bonnett, R.; McDonagh, A. F. J. Chem. Soc., Perkin Trans. 1 1973, 881.
34. See, for example: (a) Smith, K. M.; Kishore, D. Tetrahedron 1983, 39, 1841. (b) Cavaleiro, J. A. S.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1973, 2149. (c) Barnett, G. H.; Hudson, M. F.; McCombie, S. W.; Smith, K. M. J. Chem. Soc., Perkin Trans, 1 1973, 691. (d) Smith, K. M.; Sharkus, L. C.; Dallas, J. L. Biochem. Biophys. Res. Commun. 1980, 97, 1370. (e) Bonnett, R.; McDonagh, A. F. J. Chem. Soc., Perkin Trans. 1 1973, 881.
35. See, for example: (a) Smith, K. M.; Kishore, D. Tetrahedron 1983, 39, 1841. (b) Cavaleiro, J. A. S.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1973, 2149. (c) Barnett, G. H.; Hudson, M. F.; McCombie, S. W.; Smith, K. M. J. Chem. Soc., Perkin Trans, 1 1973, 691. (d) Smith, K. M.; Sharkus, L. C.; Dallas, J. L. Biochem. Biophys. Res. Commun. 1980, 97, 1370. (e) Bonnett, R.; McDonagh, A. F. J. Chem. Soc., Perkin Trans. 1 1973, 881.
36. See, for example: (a) Smith, K. M.; Kishore, D. Tetrahedron 1983, 39, 1841. (b) Cavaleiro, J. A. S.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1973, 2149. (c) Barnett, G. H.; Hudson, M. F.; McCombie, S. W.; Smith, K. M. J. Chem. Soc., Perkin Trans, 1 1973, 691. (d) Smith, K. M.; Sharkus, L. C.; Dallas, J. L. Biochem. Biophys. Res. Commun. 1980, 97, 1370. (e) Bonnett, R.; McDonagh, A. F. J. Chem. Soc., Perkin Trans. 1 1973, 881.
37. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
38. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
39. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
40. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
41. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
42. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
43. See, for example (a) Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079. (b) Bishop, J. E.; Nagy, J. O.; O'Connell, J. F.; Rapoport, H. J. Am. Chem. Soc. 1991, 113, 8024. (c) Bishop, J. E.; Dagam, S. A.; Rapoport, H. J. Org. Chem. 1989, 54, 1876. (d) Schoenleber, R. W.; Kim, Y.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 2645 and references cited therein. (e) Gossauer, A.; Hirsch, W. Liebigs Ann. Chem. 1974, 1496. (f) Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283. (g) Gossauer, A.; Weller, J.-P. Chem. Ber. 1980, 113, 1603.
44. Preliminary communications: (a) Jacobi, P. A.; Buddhu, S. C. Tetrahedron Lett. 1988, 29, 4823. (b) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231. See also: (c) Patterson, J. M.; Ferry, J. D.; Boyd, M. R. J. Am. Chem. Soc. 1973, 95, 4356.
45. Preliminary communications: (a) Jacobi, P. A.; Buddhu, S. C. Tetrahedron Lett. 1988, 29, 4823. (b) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231. See also: (c) Patterson, J. M.; Ferry, J. D.; Boyd, M. R. J. Am. Chem. Soc. 1973, 95, 4356.
46. Preliminary communications: (a) Jacobi, P. A.; Buddhu, S. C. Tetrahedron Lett. 1988, 29, 4823. (b) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231. See also: (c) Patterson, J. M.; Ferry, J. D.; Boyd, M. R. J. Am. Chem. Soc. 1973, 95, 4356.
47. (a) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
48. (b) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128.
49. See also: (c) Lockwood, R. F.; Nicholas, K. M. Tetrahedron Lett. 1977, 18, 4163. (d) Nicholas, K. M.; Nestle, M. O.; Deyferth, D. Transition Metal Organometallics; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2, p 1. (e) Evans, D. A.; Ennir, M. D., Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
50. See also: (c) Lockwood, R. F.; Nicholas, K. M. Tetrahedron Lett. 1977, 18, 4163. (d) Nicholas, K. M.; Nestle, M. O.; Deyferth, D. Transition Metal Organometallics; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2, p 1. (e) Evans, D. A.; Ennir, M. D., Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
51. See also: (c) Lockwood, R. F.; Nicholas, K. M. Tetrahedron Lett. 1977, 18, 4163. (d) Nicholas, K. M.; Nestle, M. O.; Deyferth, D. Transition Metal Organometallics; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2, p 1. (e) Evans, D. A.; Ennir, M. D., Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
52. Zimmerman, H.; Flitsch, W.; Kramer, V. Chem. Ber. 1969, 102, 3268.
53. Kakushima, M.; Hamel, P.; Frenette, R.; Rokach, J. J. Org. Chem. 1983, 48, 3214.
54. (a) Hammond, G. S.; Turro, N. J.; Leermakers, P. A. J. Phys. Chem. 1962, 66, 1144.
55. (b) Yang, N. C.; Hui, M. H.; Shold, D. M.; Turro, N. J.; Hautala, R. R.; Dawes, K.; Dalton, J. C. J. Am. Chem. Soc. 1977, 99, 3023.
56. The structure of dihydropyrromethenone 25b (E isomer) and acetylenic acid 62c were unequivocally established by single-crystal X-ray analysis: performed by Ms. Gayle Schulte, Yale University.
57. Jacobi, P. A.; Cai, G. Heterocycles 1993, 35, 1103.
58. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
59. Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856.
60. As expected, enamides 56 exhibited atropisomerism due to hindered N-N bond rotation, although each isomer had identical photochemical behavior. See, for example, ref 3, p 108.
61. (a) Pless, J. J. Org. Chem. 1974, 39, 2644.
62. (b) Clark, J. H. Chem. Rev. 1980, 80, 429.
63. (c) Morrison, H. J. Am. Chem. Soc. 1965, 87, 932.
64. (d) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6235.
65. Volante, R. P. Tetrahedron Lett. 1981, 22, 3119 and references cited therein.
66. Takai, K.; Heathcock, C. H. J. Org. Chem. 1985, 50, 3247 and references cited therein.
67. Morrison, H. J, Am. Chem. Soc. 1965, 87, 932.