Studies toward the Total Synthesis of the Oxindole Alkaloid Gelsedine: An Efficient Allene-Terminated N-Acyliminium Ion Cyclization

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8862-8867

  Beyersbergen van Henegouwen, Winfred G ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001436572     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971510n     Document Type: Article

References (39)

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22. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
23. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
24. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
25. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
26. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
27. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
28. (a) Racemic synthesis of a 7-azabicyclo[4.2.1]nonane system via N-acyliminium ion-alkyne cyclization: Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579. Other racemic syntheses of these bicyclic systems: (b) Malpass, J. R. J. Chem. Soc., Chem. Commun. 1972, 1246. (c) Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051. (d) Mondon, A.; Aumann, G.; Oelrich, E. Chem. Ber. 1972, 105, 2025. (e) Coates, J. E.; Casy, A. F. J. Org. Chem. 1974, 39, 3044. (f) Klaver, W. J.; Moolenaar, M. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805. (g) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 6729. Enantiopure synthesis of this bicyclic system: (h) Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 1581.
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