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Volumn 61, Issue 15, 1996, Pages 5013-5023

Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE;

EID: 0030017870     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960428+     Document Type: Article
Times cited : (69)

References (88)
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    • See, for example: (a) Walton, E. J. Chem. Soc. 1940, 439. (b) Schulte, K. E.; Reisch, J. Arch. Pharm. 1959, 292, 51. (c) Schulte, K. E.; Reisch, J.; Hobl, R. Arch. Pharm. 1960, 293, 687. (d) Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 490; 1969, 8, 343. (e) Scheffold, R.; Löliger, J.; Blaser, H.; Geisser, P. Helv. Chim. Acta 1975, 58, 49. (f) Gossauer, A.; Kuhne, G. Liebigs Ann. Chem. 1977, 664. (g) Cannizarro, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (h) Ribo, J. M.; Serra, X. Monatsh. Chem. 1986, 117, 185. (i) Jones, R. C. F.; Begley, M. J.; Peterson, G. E.; Sumaria, S. J. Chem. Soc, Perkin Trans. 1 1990, 1959. (j) Micklefield, J.; Mackman, R. L.; Aucken, C. J.; Beckmann, M.; Block, M. H.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Chem. Commun. 1993, 275. (k) Abell, A. D.; Oldham, M. D.; Taylor, J. M. J. Org. Chem. 1995, 60, 1214 and references cited therein. See also refs 4, 7a, 8a,e, and 2a,b.
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    • See, for example: (a) Walton, E. J. Chem. Soc. 1940, 439. (b) Schulte, K. E.; Reisch, J. Arch. Pharm. 1959, 292, 51. (c) Schulte, K. E.; Reisch, J.; Hobl, R. Arch. Pharm. 1960, 293, 687. (d) Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 490; 1969, 8, 343. (e) Scheffold, R.; Löliger, J.; Blaser, H.; Geisser, P. Helv. Chim. Acta 1975, 58, 49. (f) Gossauer, A.; Kuhne, G. Liebigs Ann. Chem. 1977, 664. (g) Cannizarro, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (h) Ribo, J. M.; Serra, X. Monatsh. Chem. 1986, 117, 185. (i) Jones, R. C. F.; Begley, M. J.; Peterson, G. E.; Sumaria, S. J. Chem. Soc, Perkin Trans. 1 1990, 1959. (j) Micklefield, J.; Mackman, R. L.; Aucken, C. J.; Beckmann, M.; Block, M. H.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Chem. Commun. 1993, 275. (k) Abell, A. D.; Oldham, M. D.; Taylor, J. M. J. Org. Chem. 1995, 60, 1214 and references cited therein. See also refs 4, 7a, 8a,e, and 2a,b.
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    • See, for example: (a) Walton, E. J. Chem. Soc. 1940, 439. (b) Schulte, K. E.; Reisch, J. Arch. Pharm. 1959, 292, 51. (c) Schulte, K. E.; Reisch, J.; Hobl, R. Arch. Pharm. 1960, 293, 687. (d) Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 490; 1969, 8, 343. (e) Scheffold, R.; Löliger, J.; Blaser, H.; Geisser, P. Helv. Chim. Acta 1975, 58, 49. (f) Gossauer, A.; Kuhne, G. Liebigs Ann. Chem. 1977, 664. (g) Cannizarro, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2316. (h) Ribo, J. M.; Serra, X. Monatsh. Chem. 1986, 117, 185. (i) Jones, R. C. F.; Begley, M. J.; Peterson, G. E.; Sumaria, S. J. Chem. Soc, Perkin Trans. 1 1990, 1959. (j) Micklefield, J.; Mackman, R. L.; Aucken, C. J.; Beckmann, M.; Block, M. H.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Chem. Commun. 1993, 275. (k) Abell, A. D.; Oldham, M. D.; Taylor, J. M. J. Org. Chem. 1995, 60, 1214 and references cited therein. See also refs 4, 7a, 8a,e, and 2a,b.
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    • Acetylenic acid 17a: Aldrich Chemical Co., Milwaukee, WI
    • (a) Acetylenic acid 17a: Aldrich Chemical Co., Milwaukee, WI.
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    • For more recent interpretations of this effect, see: (b) Parrill, A. L.; Dolata, D. P. Tetrahedron Lett. 1994, 35, 7319 and references cited therein. (c) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224.
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    • Taylor, E.C.1    Katz, A.H.2    Salgado-Zamora, H.3
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    • Amide cyclizations: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H. Tetrahedron Lett. 1985, 26, 5963. (b) Knapp, S.; Levorse, I. J. Org. Chem. 1988, 53, 4006. (c) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856. (d) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. See also refs 1 and 8c.
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    • Amide cyclizations: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H. Tetrahedron Lett. 1985, 26, 5963. (b) Knapp, S.; Levorse, I. J. Org. Chem. 1988, 53, 4006. (c) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856. (d) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. See also refs 1 and 8c.
    • (1989) J. Org. Chem. , vol.54 , pp. 5856
    • Rudisill, D.E.1    Stille, J.K.2
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    • See also refs 1 and 8c
    • Amide cyclizations: (a) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H. Tetrahedron Lett. 1985, 26, 5963. (b) Knapp, S.; Levorse, I. J. Org. Chem. 1988, 53, 4006. (c) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856. (d) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915. See also refs 1 and 8c.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3915
    • Arcadi, A.1    Cacchi, S.2    Marinelli, F.3
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    • Amine cyclizations: (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581. (b) Fukuda, Y.; Matsubara, S.; Utimoto, K. J. Org. Chem. 1991, 56, 5812 and references cited therein. (c) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
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    • Arcadi, A.1    Cacchi, S.2    Marinelli, F.3
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    • Amine cyclizations: (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581. (b) Fukuda, Y.; Matsubara, S.; Utimoto, K. J. Org. Chem. 1991, 56, 5812 and references cited therein. (c) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
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    • Fukuda, Y.1    Matsubara, S.2    Utimoto, K.3
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    • Amine cyclizations: (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581. (b) Fukuda, Y.; Matsubara, S.; Utimoto, K. J. Org. Chem. 1991, 56, 5812 and references cited therein. (c) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
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    • McGrane, P.L.1    Jensen, M.2    Livinghouse, T.3
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    • Acid cyclizations: (a) Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385. (b) Marder, T. B.; Chan, D. M.-T.; Fultz, W. C.; Calabrese, J. C.; Milstein, D. J. Chem. Soc., Chem. Commun. 1987, 1885. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976 and references cited therein. (d) Reed, P. E.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 2624.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6385
    • Chan, D.M.T.1    Marder, T.B.2    Milstein, D.3    Taylor, N.J.4
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    • Acid cyclizations: (a) Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385. (b) Marder, T. B.; Chan, D. M.-T.; Fultz, W. C.; Calabrese, J. C.; Milstein, D. J. Chem. Soc., Chem. Commun. 1987, 1885. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976 and references cited therein. (d) Reed, P. E.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 2624.
    • (1987) J. Chem. Soc., Chem. Commun. , pp. 1885
    • Marder, T.B.1    Chan, D.M.-T.2    Fultz, W.C.3    Calabrese, J.C.4    Milstein, D.5
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    • and references cited therein
    • Acid cyclizations: (a) Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385. (b) Marder, T. B.; Chan, D. M.-T.; Fultz, W. C.; Calabrese, J. C.; Milstein, D. J. Chem. Soc., Chem. Commun. 1987, 1885. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976 and references cited therein. (d) Reed, P. E.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 2624.
    • (1992) J. Org. Chem. , vol.57 , pp. 976
    • Arcadi, A.1    Burini, A.2    Cacchi, S.3    Delmastro, M.4    Marinelli, F.5    Pietroni, B.R.6
  • 66
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    • Acid cyclizations: (a) Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385. (b) Marder, T. B.; Chan, D. M.-T.; Fultz, W. C.; Calabrese, J. C.; Milstein, D. J. Chem. Soc., Chem. Commun. 1987, 1885. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976 and references cited therein. (d) Reed, P. E.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 2624.
    • (1991) J. Org. Chem. , vol.56 , pp. 2624
    • Reed, P.E.1    Katzenellenbogen, J.A.2
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    • We are grateful to Dr. Robert DeSimone for initially carrying out this reaciton
    • (b) We are grateful to Dr. Robert DeSimone for initially carrying out this reaciton.
  • 80
    • 15844418140 scopus 로고    scopus 로고
    • We are grateful to Dr. Wanjun Zheng for initially carrying out this reaction
    • (c) We are grateful to Dr. Wanjun Zheng for initially carrying out this reaction.


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