Unexpected methylation and propylation of porphyrin E-ring during the hemisynthesis of deoxophylloerythroetioporphyrin (DPEP)

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 16107-16114

  Jeandon, Christophe ^a   Ocampo, Rubén ^a   Callot, Henry J ^a  

^a CNRS   (France)

Author keywords

DPEP; Petroporphyrins; Porphyrins; Ring E alkylation; Synthesis; Triazabicyclodecene

Indexed keywords

CHLOROPHYLL A; DEOXOPHYLLOERYTHROETIOPORPHYRIN; ETIOPORPHYRIN DERIVATIVE; HETEROCYCLIC COMPOUND; PORPHYRIN; TRIAZABICYCLODECENE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; DECARBOXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HEATING; HYDROGENATION; METHYLATION; PRIORITY JOURNAL;

EID: 0030679707     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10030-8     Document Type: Article

References (28)

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2. Ocampo, R.; Callot, H.J.; Albrecht, P. Metal Complexes in Fossil Fuels (eds R.H. Filby and J.F. Branthaver), ACS Symposium Series, Vol. 344, pp. 68-73 (1987). Chicarelli, M.I.; Kaur, S.; Maxwell, J.R. Metal Complexes in Fossil Fuels (eds R.H. Filby and J.F. Branthaver), ACS Symposium Series, Vol. 344, pp. 41-67 (1987). Callot, H.J.; Ocampo, R.; Albrecht, P. Energy & Fuels 1990, 4, 635-639.
3. Ocampo, R.; Callot, H.J.; Albrecht, P. Metal Complexes in Fossil Fuels (eds R.H. Filby and J.F. Branthaver), ACS Symposium Series, Vol. 344, pp. 68-73 (1987). Chicarelli, M.I.; Kaur, S.; Maxwell, J.R. Metal Complexes in Fossil Fuels (eds R.H. Filby and J.F. Branthaver), ACS Symposium Series, Vol. 344, pp. 41-67 (1987). Callot, H.J.; Ocampo, R.; Albrecht, P. Energy & Fuels 1990, 4, 635-639.
4. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
5. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
6. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
7. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
8. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
9. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
10. Total syntheses of DPEP using preformed cyclopentenopyrroles: Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877-6879. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A. Jr; Bladel, K.A.; Feely, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J. Jr; Quinzon, D.M.; Shiner, C.M.; Watson, A. Energy & Fuels, 1990, 4, 668-674. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545-7548. Building of E-ring via double C-C bond formation: Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602-4609. E-ring formation via cyclization of a 13'-substituent: Bauder, C.; Ocampo, R.; Callot, H.J. Synlett, 1990, 335-336; Tetrahedron Lett. 1991, 32, 2537-2540; Tetrahedron, 1992, 48, 5135-5150. Clezy, P.S. Aust. J. Chem. 1991, 44, 1163-1193. Clezy, P.S.; Salek, A. Austr. J. Chem., 1996, 49, 265-272. Bong, I.C.C.; Clezy, P.S.; Fookes, C.J.R.; Prashar, J.K.; Salek, A. Austr. J. Chem., 1993, 46, 1193-1206.
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