A new synthesis of chlorins

Organic Letters

Volumn 3, Issue 6, 2001, Pages 831-834

  Jacobi, Peter A ^a   Lanz, Sandra ^a   Ghosh, Indranath ^a   Leung, Sam H ^a   Löwer, Franziska ^a   Pippin, Douglas ^a  

^a DARTMOUTH COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHLORIN; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ALDEHYDES; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORPHYRINS;

EID: 0035932603     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006983m     Document Type: Article

References (36)

1. (a) Flitsch, W. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1988; Vol. 43.
2. (b) Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327.
3. (c) Montforts, F.-P.; Glasenapp-Breiling, M. Prog. Heterocycl. Chem. 1998, 10, 1.
4. (d) Pandey, R. K.; Zheng, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 6.
5. (e) Montforts, F.-P.; Glasenapp-Breiling, M.; Kusch, D. Houben-Weyl 2000, 577.
6. (a) Prinsep, M. R.; Caplan, F. R., Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Am. Chem. Soc. 1992, 114, 385.
7. (b) Minchan, T. G.; Cook-Blumerg, L.; Kishi, Y.; Prinsep, M. R.; Moore, R. E. Angew. Chem. 1999, 111, 975, and references therein.
8. (a) Kozyrev, A. N.; Suresh, V.; Das, S.; Senge, M. O.; Shibata, M.; Dougherty, T. J.; Pandey, R. K. Tetrahedron 2000, 56, 3353, and references therein.
9. (b) Montforts, F.-P.; Meier, A.; Haake, G.; Höoper, F. Tetrahedron Lett. 1991, 32, 3481.
10. (a) Rothemund, P. J. Am. Chem. Soc. 1935, 57, 2010.
11. (b) Inhoffen, H. H.; Nolte, W. Liebigs Ann. Chem. 1969, 167.
12. Bonnett, R.; White, R. D.; Winfield, U.-J.; Berenbaum, M. C. Biochem. J. 1989, 261, 277.
13. Tomé, A. C.; Lacerda, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
14. (e) Burns, D. H.; Shi, D. C.; Lash, T. D. Chem. Commun. 2000, 299. See also refs 1 and 9a.
15. (a) Battersby, A. R.; Dutton, C. J.; Fookes, C. J. R.; Turner, S. P. D.; J. Chem. Soc., Chem. Commun. 1983, 1235.
16. (b) Battersby, A. R.; Dutton, C. J.; Fookes, C. J. R. J. Chem. Soc., Perkin Trans. 1 1988, 1569.
17. Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 5, and references therein.
18. Bishop, J. E.; O'Connell, J. F.; Rapoport, H. J. Org. Chem. 1991, 56, 5079.
19. (a) Montforts, F.-P.; Schwartz, U. M.; Liebigs Ann. Chem. 1991, 709.
20. (b) Abels, Y.; Montforts, F.-P. Tetrahedron Lett. 1997, 38, 1745, and references therein.
21. (a) Strachan, J.-P.; O'Shea, D. F.; Balasubramanian, T.; Lindsey, J. S. J. Org. Chem. 2000, 65, 3160.
22. 9a (10) Arsenault, G. P.; Bullock, E.; MacDonald, S. F. J. Am. Chem. Soc. 1960, 82, 4384.
23. (a) Jacobi, P. A.; Liu, H. J. Org. Chem. 1999, 64, 1778, and references therein. See also:
24. (b) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
25. Gossauer, A.; Hinze, R.-P. J. Org. Chem. 1978, 43, 283.
26. Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357.
27. See, for example: Bernabé, P.; Rutjes, F. P. J. T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 3561.
28. Bertz, S. H.; Eriksson, M.; Miao, G.; Snyder, J. J. Am. Chem. Soc. 1996, 118, 10906. The methyl transfer reagent was prepared by following the procedure given for the corresponding n-butyl species.
29. (a) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189.
30. (b) Srogl, J.; Liu, W.; Marshall, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 9949.
31. Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2000, 2, 3229. We gratefully acknowledge stimulating discussions with Professor Liebeskind on this subject. (d) For best results, the MeZnI reagent must be prepared by following the procedure of Fukuyama et al. (ref 16a). The reagent derived by treatment of MeMgCl with ZnI was considerably less reactive.
32. Werner, A.; Sánchez-Migallón, A.; Fruchier, A.; Elguero, J.; Fernández-Castano, C.; Foces-Foces, C.; Tetrahedron 1995, 51, 4779.
33. Arnott, D. M.; Harrison, P. J.; Henderson, G. B.; Sheng, Z.-C.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Perkin Trans. 1 1989, 265.
34. Yields refer to those obtained with the major Z-isomers of 19. The corresponding E-isomers underwent cross-coupling either very slowly or not at all.
35. See, for example: (a) Okada, K.; Saburi, K.; Nomura, K.; Tanino, H. Tetrahedron Lett. 1998, 39, 2365.
36. (b) Littler, B. J.; Miller, M. A.; Hung, C.-H.; Wagner, R. W.; O'Shea, D. F.; Boyle, P. D.; Lindsey, J. S. J. Org. Chem. 1999, 64, 1391.