Lewis acid-directed reactions of benzoquinone mono-/bis-imines: Application to syntheses of substituted β- and γ-tetrahydrocarbolines

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6135-6138

  Engler, Thomas A ^a   Wanner, Jutta ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; BETA CARBOLINE DERIVATIVE; GAMMA CARBOLINE DERIVATIVE; IMINE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030855433     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01391-9     Document Type: Article

References (61)

1. For reviews a) Perlmutter, P. "Conjugate Addition Reactions in Organic Synthesis", Tetrahedron Organic Chemistry Series Vol. 9; Pergamon: Oxford, 1992; pp. 322-330. b) Finley, K.T. In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 1", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 537. c) Allen, G.R., Jr. Org. React. 1973 20, 337-454. d) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958 1, 23-65. e) Brown, E.R. "Quinone Diimines, Monoimines and Related Compounds" In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 2", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 1231. f) Nucleophilic additions to quinones bearing electron-withdrawing groups are common.
2. For reviews a) Perlmutter, P. "Conjugate Addition Reactions in Organic Synthesis", Tetrahedron Organic Chemistry Series Vol. 9; Pergamon: Oxford, 1992; pp. 322-330. b) Finley, K.T. In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 1", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 537. c) Allen, G.R., Jr. Org. React. 1973 20, 337-454. d) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958 1, 23-65. e) Brown, E.R. "Quinone Diimines, Monoimines and Related Compounds" In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 2", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 1231. f) Nucleophilic additions to quinones bearing electron-withdrawing groups are common.
3. For reviews a) Perlmutter, P. "Conjugate Addition Reactions in Organic Synthesis", Tetrahedron Organic Chemistry Series Vol. 9; Pergamon: Oxford, 1992; pp. 322-330. b) Finley, K.T. In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 1", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 537. c) Allen, G.R., Jr. Org. React. 1973 20, 337-454. d) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958 1, 23-65. e) Brown, E.R. "Quinone Diimines, Monoimines and Related Compounds" In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 2", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 1231. f) Nucleophilic additions to quinones bearing electron-withdrawing groups are common.
4. For reviews a) Perlmutter, P. "Conjugate Addition Reactions in Organic Synthesis", Tetrahedron Organic Chemistry Series Vol. 9; Pergamon: Oxford, 1992; pp. 322-330. b) Finley, K.T. In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 1", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 537. c) Allen, G.R., Jr. Org. React. 1973 20, 337-454. d) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958 1, 23-65. e) Brown, E.R. "Quinone Diimines, Monoimines and Related Compounds" In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 2", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 1231. f) Nucleophilic additions to quinones bearing electron-withdrawing groups are common.
5. For reviews a) Perlmutter, P. "Conjugate Addition Reactions in Organic Synthesis", Tetrahedron Organic Chemistry Series Vol. 9; Pergamon: Oxford, 1992; pp. 322-330. b) Finley, K.T. In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 1", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 537. c) Allen, G.R., Jr. Org. React. 1973 20, 337-454. d) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958 1, 23-65. e) Brown, E.R. "Quinone Diimines, Monoimines and Related Compounds" In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 2", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 1231. f) Nucleophilic additions to quinones bearing electron-withdrawing groups are common.
6. For reviews a) Perlmutter, P. "Conjugate Addition Reactions in Organic Synthesis", Tetrahedron Organic Chemistry Series Vol. 9; Pergamon: Oxford, 1992; pp. 322-330. b) Finley, K.T. In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 1", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 537. c) Allen, G.R., Jr. Org. React. 1973 20, 337-454. d) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958 1, 23-65. e) Brown, E.R. "Quinone Diimines, Monoimines and Related Compounds" In "The Chemistry of the Quinonoid Compounds, Vol. 2, Part 2", Patai, S.; Rappaport, Z., Eds.; Wiley:Chichester, 1988; p. 1231. f) Nucleophilic additions to quinones bearing electron-withdrawing groups are common.
7. a) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1977, 4041-4044.
8. b) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1978, 2589-2592.
9. c) Ipaktschi, J.; Heydari, A. Angew. Chem. Int. Ed. Engl. 1992 31, 313-314.
10. d) Naruta, Y. J. Am. Chem. Soc. 1980 102, 3774-3783.
11. For reviews and summaries of related papers, see e) Fleming, I, Dunogués, J.; Smithers, R. Org. React. 1989 37, 57-575. f) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1992 71, 125-131. g) Naruta, Y.; Maruyama, K. In "The Chemistry of Quinonoid Compounds, Vol. II" Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester; Chapter 8.
12. For reviews and summaries of related papers, see e) Fleming, I, Dunogués, J.; Smithers, R. Org. React. 1989 37, 57-575. f) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1992 71, 125-131. g) Naruta, Y.; Maruyama, K. In "The Chemistry of Quinonoid Compounds, Vol. II" Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester; Chapter 8.
13. For reviews and summaries of related papers, see e) Fleming, I, Dunogués, J.; Smithers, R. Org. React. 1989 37, 57-575. f) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1992 71, 125-131. g) Naruta, Y.; Maruyama, K. In "The Chemistry of Quinonoid Compounds, Vol. II" Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester; Chapter 8.
14. a) Mukaiyama, T.; Sagawa, Y.; Kobayashi, S. Chem. Lett. 1987, 2169-2172.
15. b) Neville, D.; Murphy, W.S. Tetrahedron Lett. 1996 37, 5221-5224.
16. c) Bernatek, E. Acta Chem. Scand. 1953 7, 677-681.
17. d) Bernatek, E.; Ledaal, T. ibid. 1958 12, 2053-2054.
18. e) Grinev, A.N.; Pan, B.-K.; Terent'ev, A.P. Zhur. Obschei Khim. 1957 27, 1087-1089; Chem. Abstr. 1958 52, 3761e.
19. e) Grinev, A.N.; Pan, B.-K.; Terent'ev, A.P. Zhur. Obschei Khim. 1957 27, 1087-1089; Chem. Abstr. 1958 52, 3761e.
20. f) Giza, C.A.; Hinman, R.L. J. Org. Chem. 1964 29, 1453-1461.
21. g) Brannock, K.C.; Burpitt, R.D. U.S. Patent 3,285,937, 1966; Chem. Abstr. 1967 66, 37762p.
22. g) Brannock, K.C.; Burpitt, R.D. U.S. Patent 3,285,937, 1966; Chem. Abstr. 1967 66, 37762p.
23. See also, h) Ipaktschi, J.; Heydari, A. Chem. Ber. 1992, 125, 1513-1515. i) Danishefsky, S.; McKee, R.; Singh, R.K. J. Org. Chem. 1976 41, 2934-2935.
24. See also, h) Ipaktschi, J.; Heydari, A. Chem. Ber. 1992, 125, 1513-1515. i) Danishefsky, S.; McKee, R.; Singh, R.K. J. Org. Chem. 1976 41, 2934-2935.
25. a) Engler, T.A.; Combrink, K.D.; Letavic, M.A.; Lynch, K.O., Jr.; Ray, J.E. J. Org. Chem. 1994, 59, 6567-6587.
26. b) Engler, T.A.; Gfesser, G.A.; Draney, B.W. J. Org. Chem. 1995, 60, 3700-06.
27. c) Engler, T.A.; Meduna, S.P.; LaTessa, K.O.; Chai, W. J. Org. Chem., 1996, 61, 8598-8603.
28. d) Engler, T.A.; Chai, W. Tetrahedron Lett., 1996, 37, 6969-6970.
29. e) Murphy, W.S.; Neville, D. Tetrahedron Lett. 1996 37, 9397-9340.
30. a) Engler, T.A.; Wei, D.; Letavic, M.A.; Combrink, K.D.; Reddy, J.P. J. Org. Chem. 1994, 59, 6588-6599.
31. b) Engler, T.A.; Chai, W.; LaTessa, K.O J. Org. Chem., 1996, 61, 9297-9308.
32. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
33. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
34. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
35. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
36. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
37. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
38. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
39. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
40. Adams and Boger have reported regiocontrolled additions to quinone imines and Reusch, Valenta and Hendrickson have explored regioselective Lewis acid-activation of quinones for Diels-Alder reactions. For leading references, see reference Id and a) Boger, D.L.; Zarrinmayeh, H. J. Org. Chem. 1990 55, 1379-1390. The regioselective addition of HCl to quinone bisimides has been questioned, b) Holmes, T.J., Jr.; Lawton, R.G. J. Org. Chem. 1983 48, 3146. c) Tou, J.S.; Reusch, W. J. Org. Chem. 1980, 45, 5012- 5014. d) Dickinson, R.A.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. e) Stojanac, Z.; Dickinson, R.A.; Stojanac, N.; Woznow, R.J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. f) Das, J.; Kubela, R.; MacAlpine, G.A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. g) Hendrickson, J.B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. h) Hendrickson, J.B.; Haestier, A.M.; Stieglitz, S.G.; Foxman, B.M. New J. Chem. 1990, 14, 689-693. For another report, i) Engler, T.A.; Letavic, M.A.; Lynch, K.O., Jr.; Takusagawa, F. J. Org. Chem. 1994,59,1179-1183.
41. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
42. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
43. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
44. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
45. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
46. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
47. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
48. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
49. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
50. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
51. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
52. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
53. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
54. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
55. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
56. For reviews and leading references, a) for β-carbolines: Love, B. Org. Prep Proceed. Int. 1996 28, 1-64. Cox, E.D.; Cook, J.M. Chem. Rev. 1995 95, 1797-1842. Baker, B.J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Pergamon: New York, 1996; Vol. 10. Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp. 135-170. b) for γ-carbolines: Gribble, G. W. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7. c) for δ-carbolines, Desarbre, E.; Mérour, J.-Y. Synthesis 1997 73-78. For examples of recent reports, d) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997 53, 1593-1606. e) Audia, J.E.; Evrard, D.A.; Murdoch, G.R.; Droste, J.J.; Nissen, J.S.; Schenck, K.W.; Fludzinski, P.; Lucaites, V.L.; Nelson, D.L.; Cohen, M.L. J. Med. Chem. 1996 39, 2773-2780. f) Ezquerra, J.; Lama, C.; Pastor, A.; Alvarez, P.; Vaquero, J.J.; Prowse, W.G. Tetrahedron Lett. 1996 37, 5813-5816. g) Mohan, R.; Chou, Y.-L.; Morrissey, M.M. ibid. 1996 37, 3963-3966. h) Mayer, J.P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C.M.; Goodman, B.A.; Herrera, C.J. ibid. 1996 37, 5633-5636. i) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. ibid. 1996 37, 3071-3074. j) Li, J.-H.; Snyder, J.K. ibid. 1994 35, 1485-1488. k) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993 49, 3325-3342. l) Dekhane, M.; Dodd, R.H. ibid. 1994 50, 6299-6306. m) Chen, C.-y.; Lieberman, D.R.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. J. Org. Chem. 1997 62, 2676-2677.
57. a) Barbot, F.; Miginiac, P. Helv. Chim. Acta 1979 62, 1451-1457. See also,
58. b) Faja, M.; Reese, C.B.; Song, Q.; Zhang, P.-Z. J. Chem. Soc., Perkin 1 1997 101-104.
59. 13C NMR, IR and mass spectral data, including exact mass and/or elemental analysis.
60. For examples, see references 4 and 5.
61. For a summary of methods, see Sundberg, R.J. Indoles, Academic: San Diego, 1996.