-
1
-
-
0017032571
-
-
For leading references regarding isolation, characterization, and biosynthesis of ibophyllidine alkaloids, see: (a) Khuong-Huu, F.; Cesario, M.; Guilhem, J.; Goutarel, R. Tetrahedron 1976, 32, 2539. (b) Kan, C.; Husson, H.-P.; Jacquemin, H.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 55. (c) Kan, C.; Husson, H.-P.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 3363. (d) Kuehne, M. E.; Pitner, J. B. J. Org. Chem. 1989, 54, 4553. (e) Saxton, J. E. The Ibogamine-Catharanthine Group. In Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds, Taylor, E. C., Ed.; John Wiley: Chichester, 1994; Vol. 25, pp 487-521.
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Tetrahedron
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Khuong-Huu, F.1
Cesario, M.2
Guilhem, J.3
Goutarel, R.4
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2
-
-
0005493164
-
-
For leading references regarding isolation, characterization, and biosynthesis of ibophyllidine alkaloids, see: (a) Khuong-Huu, F.; Cesario, M.; Guilhem, J.; Goutarel, R. Tetrahedron 1976, 32, 2539. (b) Kan, C.; Husson, H.-P.; Jacquemin, H.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 55. (c) Kan, C.; Husson, H.-P.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 3363. (d) Kuehne, M. E.; Pitner, J. B. J. Org. Chem. 1989, 54, 4553. (e) Saxton, J. E. The Ibogamine-Catharanthine Group. In Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds, Taylor, E. C., Ed.; John Wiley: Chichester, 1994; Vol. 25, pp 487-521.
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Tetrahedron Lett.
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Kan, C.1
Husson, H.-P.2
Jacquemin, H.3
Kan, S.-K.4
Lounasmaa, M.5
-
3
-
-
0005512456
-
-
For leading references regarding isolation, characterization, and biosynthesis of ibophyllidine alkaloids, see: (a) Khuong-Huu, F.; Cesario, M.; Guilhem, J.; Goutarel, R. Tetrahedron 1976, 32, 2539. (b) Kan, C.; Husson, H.-P.; Jacquemin, H.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 55. (c) Kan, C.; Husson, H.-P.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 3363. (d) Kuehne, M. E.; Pitner, J. B. J. Org. Chem. 1989, 54, 4553. (e) Saxton, J. E. The Ibogamine-Catharanthine Group. In Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds, Taylor, E. C., Ed.; John Wiley: Chichester, 1994; Vol. 25, pp 487-521.
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Tetrahedron Lett.
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Kan, C.1
Husson, H.-P.2
Kan, S.-K.3
Lounasmaa, M.4
-
4
-
-
0024426332
-
-
For leading references regarding isolation, characterization, and biosynthesis of ibophyllidine alkaloids, see: (a) Khuong-Huu, F.; Cesario, M.; Guilhem, J.; Goutarel, R. Tetrahedron 1976, 32, 2539. (b) Kan, C.; Husson, H.-P.; Jacquemin, H.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 55. (c) Kan, C.; Husson, H.-P.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 3363. (d) Kuehne, M. E.; Pitner, J. B. J. Org. Chem. 1989, 54, 4553. (e) Saxton, J. E. The Ibogamine-Catharanthine Group. In Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds, Taylor, E. C., Ed.; John Wiley: Chichester, 1994; Vol. 25, pp 487-521.
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Kuehne, M.E.1
Pitner, J.B.2
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5
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0005422544
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Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. Taylor, E. C., Ed.; John Wiley: Chichester
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For leading references regarding isolation, characterization, and biosynthesis of ibophyllidine alkaloids, see: (a) Khuong-Huu, F.; Cesario, M.; Guilhem, J.; Goutarel, R. Tetrahedron 1976, 32, 2539. (b) Kan, C.; Husson, H.-P.; Jacquemin, H.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 55. (c) Kan, C.; Husson, H.-P.; Kan, S.-K.; Lounasmaa, M. Tetrahedron Lett. 1980, 21, 3363. (d) Kuehne, M. E.; Pitner, J. B. J. Org. Chem. 1989, 54, 4553. (e) Saxton, J. E. The Ibogamine-Catharanthine Group. In Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds, Taylor, E. C., Ed.; John Wiley: Chichester, 1994; Vol. 25, pp 487-521.
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Saxton, J.E.1
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6
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The biogenetic numbering (Le Men, J.; Taylor, W. I. Exptrientia 1965, 21, 508) is used throughout this paper only for pentacyclic compounds.
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, vol.21
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Le Men, J.1
Taylor, W.I.2
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8
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0002038735
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Pentacyclic Strychnos Indole Alkaloids
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Atta-ur-Rahman, Ed.; Eisevier: Amsterdam
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(a) Bosch, J.; Bonjoch, J. Pentacyclic Strychnos Indole Alkaloids. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Eisevier: Amsterdam, 1988; Vol. 1, pp 31-88.
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Cordell, G. A., Ed.; Academic Press: New York
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(b) Bosch, J.; Bonjoch, J.; Amat, M. Strychnos Alkaloids. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp 75-189.
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(a) Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem. 1981, 46, 2002.
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Bohnert, J.C.3
Motyka, L.4
Oliver-Smith, D.5
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(c) Barsi, M.-C.; Das, B. C.; Fourrey, J.-L.; Sundaramoorthi, R. J. Chem. Soc., Chem. Commun. 1985, 88.
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(d) Jegham, S.; Fourrey, J.-L.; Das, B. C. Tetrahedron Lett. 1989, 30, 1959.
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14
-
-
16044368498
-
-
note
-
(a) Prior syntheses of (±)-deethylibophyllidine: refs 1d, 5a, and 5c.
-
-
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15
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0028228136
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(b) Preliminary communication: Catena, J.; Valls, N.; Bosch, J.; Bonjoch, J. Tetrahedron Lett. 1994, 35, 4433.
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Catena, J.1
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Bonjoch, J.4
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37049085728
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(c) Recently, we have described another synthetic approach to this target: Fernàndez, J.-C.; Valls. N.; Bosch, J.; Bonjoch, J. J. Chem. Soc., Chem. Commun. 1985, 2317.
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Fernàndez, J.-C.1
Valls, N.2
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Bonjoch, J.4
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17
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0023852740
-
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For the previous synthesis of perhydropyrrolo[3,2,1-h,i]indoles functionalized at the carbocyclic ring, see: (a) Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81. (b) Valls, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1992, 57, 2508.
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Lathbury, D.C.1
Parsons, P.J.2
Pinto, I.3
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18
-
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16044369099
-
-
For the previous synthesis of perhydropyrrolo[3,2,1-h,i]indoles functionalized at the carbocyclic ring, see: (a) Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81. (b) Valls, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1992, 57, 2508.
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Valls, N.1
Bonjoch, J.2
Bosch, J.3
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19
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0021030718
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For the only previously described synthetic strategy, see: Magnus, P. D.; Exon, C.; Sear, N. L. Tetrahedron 1983, 39, 3725.
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(1983)
Tetrahedron
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, pp. 3725
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Magnus, P.D.1
Exon, C.2
Sear, N.L.3
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20
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77957033352
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Brossi, A., Ed.; Academic Press: New York
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For reviews: (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, pp 251-376. (b) Lewis, J. R. Nat. Prod. Rep. 1992, 9, 183.
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Martin, S.F.1
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For reviews: (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, pp 251-376. (b) Lewis, J. R. Nat. Prod. Rep. 1992, 9, 183.
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Lewis, J.R.1
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By Birch reduction of 4-methoxyphenethylamines: (a) Ueda, N.; Tokuyama, T.; Sakan, T. Bull. Chem. Soc. Jpn. 1966, 39, 2012. (b) Sawlewicz, P.; Smulkowski, M.; Sowinski, P.; Borowaki, E. Pol. J. Chem. 1978, 52, 219.
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Bull. Chem. Soc. Jpn.
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Ueda, N.1
Tokuyama, T.2
Sakan, T.3
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23
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16044366849
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By Birch reduction of 4-methoxyphenethylamines: (a) Ueda, N.; Tokuyama, T.; Sakan, T. Bull. Chem. Soc. Jpn. 1966, 39, 2012. (b) Sawlewicz, P.; Smulkowski, M.; Sowinski, P.; Borowaki, E. Pol. J. Chem. 1978, 52, 219.
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Sawlewicz, P.1
Smulkowski, M.2
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Borowaki, E.4
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24
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0025091009
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3 complex of a 2-methoxycyclohexadiene cation: Bös, M.; Burkard, W. P.; Moreau, J.-L.; Schönholzer, P. Helv. Chim. Acta 1990, 73, 932.
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Burkard, W.P.2
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Schönholzer, P.4
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25
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0023690543
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By intramolecular photocycloaddition and retro-Mannich fragmentation of acyclic tertiary vinylogous amides: Winkler, J. D.; Muller, C. L.; Scott, R. D. J. Am. Chem. Soc. 1988, 110, 4831.
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Scott, R.D.3
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26
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0009610565
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For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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Bryson, T.A.1
Gammill, R.B.2
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27
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37049117807
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For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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J. Chem. Soc., Perkin Trans. 1
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Iida, H.1
Aoyagi, S.2
Kibayashi3
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28
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84985122356
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For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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Synthesis
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Iida, H.1
Yuasa, Y.2
Kibayashi, C.3
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29
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0026758519
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For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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Tetrahedron Lett.
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Michael, J.P.1
Howard, A.S.2
Katz, R.B.3
Zwane, M.I.4
-
30
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0026674070
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-
For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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Tetrahedron Lett.
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Michael, J.P.1
Zwane, M.I.2
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31
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0021038169
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For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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Higashiyama, H.1
Honda, T.2
Otomasu, H.3
Kametani, T.4
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32
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16044374795
-
-
For approaches leading to 1,2,3,3a,4,5-hexahydroindol-6-ones, see: (a) from 1,3-cyclohexanedione, Bryson, T. A.; Gammill, R. B. Tetrahedron Lett. 1974, 3963. (b) From 6-methoxyindoline, Iida, H.; Aoyagi, S.; Kibayashi J. Chem. Soc., Perkin Trans. 1 1975, 2502. Iida, H.; Yuasa, Y.; Kibayashi, C. Synthesis 1977, 879. From pyrrolidine-2-thiones, Michael, J. P.; Howard, A. S.; Katz, R. B.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4751. Michael, J. P.; Zwane, M. I. Tetrahedron Lett. 1992, 33, 4755. For the reduction to octahydroderivatives: Higashiyama, H.; Honda, T.; Otomasu, H.; Kametani, T. Planta Med. 1983, 48, 268. Ito, K.; Naruma, M.; Furukawa, H. J. Chem. Soc., Chem. Commun. 1975, 681.
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Ito, K.1
Naruma, M.2
Furukawa, H.3
-
33
-
-
16044365351
-
-
note
-
All synthetic compounds are racemic. The schemes depict only the enantiomer bearing the natural configuration at C-14.
-
-
-
-
34
-
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0000179169
-
-
10a For the synthesis of hexahydroindol-6-ones by hypervalent iodine oxidation of tyramine derivatives, see: (a) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435. (b) Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739.
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Yakura, T.5
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35
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0030050808
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10a For the synthesis of hexahydroindol-6-ones by hypervalent iodine oxidation of tyramine derivatives, see: (a) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435. (b) Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739.
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Goldstein, D.M.1
Wipf, P.2
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39
-
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16044362067
-
-
note
-
On the contrary, when the acylation was carried out in the Schotten-Baumann conditions, acylated but not cyclized compound 3 was isolated (see Experimental Section).
-
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40
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0003232070
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(a) Wu, P.-L.; Chu, M.; Fowler, F. W. J. Org. Chem. 1988, 53, 963.
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Bonjoch, J.; Casamitjana, N.; Quirante, J.; Rodríguez, M.; Bosch, J. J. Org. Chem. 1987, 52, 267.
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46
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For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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Stork, G.1
Dolfini, J.E.2
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47
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0013787215
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For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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Ban, Y.1
Sato, Y.2
Inoue, I.3
Nagai, M.4
Oishi, T.5
Terashima, M.6
Yonemitsu, O.7
Kanaoka, Y.8
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48
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0014701207
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For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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Inoue, I.1
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49
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0142173074
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For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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Klioze, S.S.1
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50
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0017373420
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For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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Lawton, G.1
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Smith, A.J.3
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51
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37049112704
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For indolization upon the methine carbon in the Aspidosperma series, see: (a) Stork. G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872. (b) Ban, Y.; Sato, Y.; Inoue, I.; Nagai, M.; Oishi, T.; Terashima, M.; Yonemitsu, O.; Kanaoka, Y. Tetrahedron Lett. 1966, 2261. (c) Inoue, I.; Ban, Y. J. Chem. Soc (C) 1970, 602. (d) Klioze, S. S.; Darmory, F. P. J. Org. Chem. 1975, 40, 1588. (e) Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641. (f) Pearson, A. J.; Rees, D. C. J. Chem. Soc., Perkin Trans. 1 1982, 2467.
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Crabb, T. A.; Newton, R. F.; Jackson, D. Chem. Rev. 1971, 71, 109.
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54
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See also ref 23e
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(a) For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones in this field, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523. See also ref 23e.
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Ban, Y.1
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55
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(b) For a discussion about the stereochemical factors influencing the regiochemical course of Fischer indole synthesis, see: Freter, K.; Fuchs, V.; Pitner, T. P. J. Org. Chem. 1983, 48, 4593.
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56
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0004047925
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For conformational analysis of the cis-octahydroindole, see: Mokotoff, M.; Hill, S. T. J. Heterocycl. Chem. 1988, 25, 65. For the conformational preference in 3a-aryloctahydroindol-6-ones (i.e. mesembrine), see: Jeffs, P. W.; Hawks, R. L.; Farrier, D. S. J. Am. Chem. Soc. 1969, 91, 3831. Sánchez, I. H.; Larraza, M.-I.; Flores, H. J.; Díaz, E. Heterocycles 1985, 23, 593.
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57
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For conformational analysis of the cis-octahydroindole, see: Mokotoff, M.; Hill, S. T. J. Heterocycl. Chem. 1988, 25, 65. For the conformational preference in 3a-aryloctahydroindol-6-ones (i.e. mesembrine), see: Jeffs, P. W.; Hawks, R. L.; Farrier, D. S. J. Am. Chem. Soc. 1969, 91, 3831. Sánchez, I. H.; Larraza, M.-I.; Flores, H. J.; Díaz, E. Heterocycles 1985, 23, 593.
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58
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0004047925
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For conformational analysis of the cis-octahydroindole, see: Mokotoff, M.; Hill, S. T. J. Heterocycl. Chem. 1988, 25, 65. For the conformational preference in 3a-aryloctahydroindol-6-ones (i.e. mesembrine), see: Jeffs, P. W.; Hawks, R. L.; Farrier, D. S. J. Am. Chem. Soc. 1969, 91, 3831. Sánchez, I. H.; Larraza, M.-I.; Flores, H. J.; Díaz, E. Heterocycles 1985, 23, 593.
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59
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0025123570
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N-Benzyliodoacetamide was prepared from benzylamine and chloroacetyl chloride and later treatment of the resulting chlorocetamide with sodium iodide in 2-butanone according to Dufour, M.; Gramain, J.-C.; Husson, H.-P.; Sinibaldi, M.-E.; Troin, Y. J. Org. Chem. 1990, 55, 5483.
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Troin, Y.5
-
60
-
-
16044366982
-
-
note
-
Operating with AcOH/NaOAc or EtOH/HCl instead of AcOH neat, the ratio of indole 17 increases and is the major product in the indolization.
-
-
-
-
61
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0025234942
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For studies on the regioselectivity in the Fischer indolization of β-amino ketones, see: Bonjoch, J.; Casamitjana, N.; Gràcia, J.; Úbeda, M.-C.; Bosch, J. Tetrahedron Lett. 1990, 31, 2449.
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Bonjoch, J.1
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Úbeda, M.-C.4
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62
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33748542524
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The influence of the A 1,3 strain (Johnson, F. Chem. Rev. 1968, 68, 375) caused by the amide linkage in this conformational change was suggested by a reviewer. Also the difference in regioselectivity in the Fischer indole synthesis of hydroindolones could be accounted for considering that it occurs through the enehydrazine that minimizes the A 1,3 strain.
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Chem. Rev.
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Johnson, F.1
-
63
-
-
16044368445
-
-
note
-
13C NMR, see Table 2.
-
-
-
-
64
-
-
0027716570
-
-
For a successful formation of C-6/C-7 bond by this coupling-type in β-unsubstituted indoles, see: Bennasar, M.-L.; Zulaica, E.; Jiménez, J.-M.; Bosch, J. J. Org. Chem. 1993, 58, 7756.
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Bennasar, M.-L.1
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Jiménez, J.-M.3
Bosch, J.4
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65
-
-
16044370864
-
-
note
-
3, HMQC) 18.4 (C-4), 23.6 (C-5), 26.4 (C-3), 29.7 (C-11), 36.7 (C-3a), 46.4 (C-2), 54.8 (C-10c), 109.6 (C-7), 110.0 (C-10b), 119.0 (C-9), 122.7 (C-8), 124.3 (C-10a), 126.2 (C-10), 131.2 (C-5a), 135.2 (C-6a), 170.4 (C-12).
-
-
-
-
66
-
-
0009464699
-
-
A similar result has been observed in the Strychnos series: Bosch, J.; Amat, M.; Sanfeliu, E.; Miranda, M.-A. Tetrahedron 1985, 41, 2557.
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Bosch, J.1
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Miranda, M.-A.4
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67
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0001549820
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Trost, B. M., Ed.; Pergamon: Oxford
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The Pummerer rearrangement has emerged as a versatile and effective method for the generation of cationic reactive intermediates from sulfoxide precursors. For recent reviews, see: (a) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947. (b) Kennedy, M.; McKervey, M. A. Ibid. Vol. 7, pp 193-216. (c) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
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Grierson, D.S.1
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68
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0000458709
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The Pummerer rearrangement has emerged as a versatile and effective method for the generation of cationic reactive intermediates from sulfoxide precursors. For recent reviews, see: (a) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947. (b) Kennedy, M.; McKervey, M. A. Ibid. Vol. 7, pp 193-216. (c) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
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Kennedy, M.1
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69
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0001272894
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The Pummerer rearrangement has emerged as a versatile and effective method for the generation of cationic reactive intermediates from sulfoxide precursors. For recent reviews, see: (a) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947. (b) Kennedy, M.; McKervey, M. A. Ibid. Vol. 7, pp 193-216. (c) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
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De Lucchi, O.1
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(a) Amat, M.; Alvarez, M.; Bonjoch, J.; Casamitjana, N.; Gràcia, J.; Lavilla, R.; Garcías, X.; Bosch, J. Tetrahedron Lett. 1990, 31, 3453.
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Yoshida, K.; Nakajima, S.; Wakamatsu, T.; Ban, Y.; Shibasaki, M. Heterocycles 1988, 27, 1167.
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37049094920
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40c,d upon phenyl vinyl sulfoxide, see: (a) Abbott, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 492. (b) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1986, 27, 2603. (c) Lee, A. W. M.; Chan, W. H.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 309. (d) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
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Abbott, D.J.1
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0343759319
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Maignan, C.1
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37049071768
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Lee, A.W.M.1
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0026699037
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40c,d upon phenyl vinyl sulfoxide, see: (a) Abbott, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1976, 492. (b) Maignan, C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1986, 27, 2603. (c) Lee, A. W. M.; Chan, W. H.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 309. (d) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
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Craig, D.1
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79
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16044375120
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note
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Compound 30 was a diastereomeric mixture at sulfur, which could not be separated at this stage.
-
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80
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16044370300
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note
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42d
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82
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0030000558
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(c) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. Tetrahedron Lett. 1996, 37, 3071.
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Besselièvre, R.; Husson, H.-P. Tetrahedron 1981, 37, Suppl. No. 1, 241.
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