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Volumn 67, Issue 25, 2002, Pages 8726-8743

Total synthesis and biological evaluation of Amaryllidaceae alkaloids: Narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives

Author keywords

[No Author keywords available]

Indexed keywords

BIOCATALYSTS; CELLS; DERIVATIVES; ENZYMES; SYNTHESIS (CHEMICAL);

EID: 0037073868     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020129m     Document Type: Article
Times cited : (189)

References (149)
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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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    • 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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    • (b) We have reported the synthesis of 7-deoxypancratistatin by the intramolecular aziridine opening at many occasions at conferences. The proceedings of the Heterocyclic Congress in Vienna, August 1999, were published before the erroneous assignment was observed: Hudlicky, T. J. Heterocycl. Chem. 2000, 37, 535. The incorrectly assigned structure as well as reasons for not detecting this error has been reported as a full paper (ref 46a). The major lesson learned from these endeavor was the recognition that structure assignment of highly similar compounds is very difficult by NMR techniques alone.
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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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