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note
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Preliminary disclosures for narciclasine, see ref 91; for ent-7-deoxypancratistatin, see ref 10n, and for epi-7-deoxypancratistatin, see ref 50.
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77957033352
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(b) Polt, R. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 3, p 109.
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ref 4. Lycoricidine
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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10
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0014328273
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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Okamoto, T.1
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0001125112
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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Piozzi, F.1
Fuganti, C.2
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Ceriotti, G.4
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2242465742
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See ref 6b
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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13
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0021194467
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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Wakamiya, T.1
Nakamoto, W.H.2
Shiba, T.3
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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0000794608
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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0000484955
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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Isolation and structure elucidation of Amaryllidaceae alkaloids: Lycorine: (a) ref 4. Lycoricidine: (b) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860. Narciclasine: (c) Piozzi, F.; Fuganti, C.; Mondelli, R.; Ceriotti, G. Tetrahedron 1968, 24, 1119. (d) See ref 6b. (e) Wakamiya, T.; Nakamoto, W. H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (f) Trimino Ayllon, Z.; Ramos Martinez, I.; Iglesias Perez, C.; Spengler Salabarria, I.; Velez Castro, H. Rev. Cubana Farm. 1999, 23, 155. (g) Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.; Lanzeta, R.; Seif El Din, A. Phytochemistry 1991, 30, 3445. 7-Deoxypancratistatin: (h) Ghosal, S.; Singh, S.; Kumar, Y.; Srivastava, R. S. Phytochemistry 1989, 28, 611. Pancratistatin: (i) Pettit, G. R.; Gaddamidi, V.; Cragg, G. M.; Herald, D. L.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1994, 1693. (j) Pettit, G. R.; Backhaus, R. A.; Boettner, F. E. J. Nat. Prod. 1995, 58, 37.
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After a personal communication with Dr. Pulley, we obtained the correct procedure that used LiCl in DMF at 120°C for 2 h, not LiI as reported in ref 10c.
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note
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13C NMR spectra were obtained on a Varian 300 or 500 MHz instrument. Proton and carbon chemical shifts are reported in ppm, relative to chloroform (7.24 and 77.23 ppm), respectively. Mass spectra were recorded on a Finnigan-Matt 95 instrument.
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