Stereocontrolled elaboration of quaternary carbon centers through the asymmetric Michael-type alkylation of chiral imines/secondary enamines: Enantioselective synthesis of (+)-vincamine

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3890-3901

  Desmaële, Didier ^a   Mekouar, Khalid ^a   D'Angelo, Jean ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

VINCAMINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030754465     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9622690     Document Type: Article

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49. Semisynthetic routes to vincamine. (a) Hugel, G.; Lévy, J.; Le Men, J. C. R. Acad. Sc. 1972, 274, 1350-1352. (b) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (c) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem Soc., Chem. Commun. 1981, 908-909. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073.
50. Semisynthetic routes to vincamine. (a) Hugel, G.; Lévy, J.; Le Men, J. C. R. Acad. Sc. 1972, 274, 1350-1352. (b) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (c) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem Soc., Chem. Commun. 1981, 908-909. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073.
51. Semisynthetic routes to vincamine. (a) Hugel, G.; Lévy, J.; Le Men, J. C. R. Acad. Sc. 1972, 274, 1350-1352. (b) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (c) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem Soc., Chem. Commun. 1981, 908-909. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073.
52. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
53. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
54. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
55. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
56. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
57. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
58. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
59. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
60. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
61. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
62. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
63. Syntheses of alkaloids related to vincamine (selected papers). Eburnamonine: (a) Bartlett, M. F.; Taylor, W. I. J. Am. Chem. Soc. 1960, 82, 5941-5946. (b) See ref 11c. (c) Buzas, A.; Herisson, C.; Lavielle, G. C. R. Acad. Sc. 1976, 283, 763-765. (d) Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893-4894. (e) Bölsing, E.; Klatte, F.; Rosentreter, U.; Winterfeldt, E. Chem. Ber. 1979, 112, 1902-1912. (f) Buzas, A.; Jacquet, J.-P.; Lavielle, G. J. Org. Chem. 1980, 45, 32-34. (g) Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206. (h) Wenkert, E. ; Haus, T. D. J.; Kwart, L. D.; Magnusson, G.; Showalter, H. D. H. Tetrahedron 1981, 37, 4017-4025. (i) Magnus, P.; Pappalardo, P.; Southwell, I. Ibid. 1986,42, 3215-3222. (j) Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521, (k) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198. (l) Da Silva Goes, A.; Ferroud, C.; Santamaria, J. Tetrahedron Lett. 1995, 36, 2235-2238.
64. Homoeburnamonine: (m) See ref 11d, e. (n) Laronze, J.; Laronze, J. Y.; Lévy, J.; Le Men, J. Bull. Soc. Chim. Fr. 1977, 1195-1206. (o) Buzas, A.; Retourne, C.; Jacquet, J. P.; Lavielle, G. Tetrahedron 1978, 34, 3001-3004. (p) Szabó, L.; Sápi, J.; Nógrádi, K.; Kalaus, G.; Szántay, C. Ibid. 1983, 39, 3749-3753.
65. Homoeburnamonine: (m) See ref 11d, e. (n) Laronze, J.; Laronze, J. Y.; Lévy, J.; Le Men, J. Bull. Soc. Chim. Fr. 1977, 1195-1206. (o) Buzas, A.; Retourne, C.; Jacquet, J. P.; Lavielle, G. Tetrahedron 1978, 34, 3001-3004. (p) Szabó, L.; Sápi, J.; Nógrádi, K.; Kalaus, G.; Szántay, C. Ibid. 1983, 39, 3749-3753.
66. Homoeburnamonine: (m) See ref 11d, e. (n) Laronze, J.; Laronze, J. Y.; Lévy, J.; Le Men, J. Bull. Soc. Chim. Fr. 1977, 1195-1206. (o) Buzas, A.; Retourne, C.; Jacquet, J. P.; Lavielle, G. Tetrahedron 1978, 34, 3001-3004. (p) Szabó, L.; Sápi, J.; Nógrádi, K.; Kalaus, G.; Szántay, C. Ibid. 1983, 39, 3749-3753.
67. Homoeburnamonine: (m) See ref 11d, e. (n) Laronze, J.; Laronze, J. Y.; Lévy, J.; Le Men, J. Bull. Soc. Chim. Fr. 1977, 1195-1206. (o) Buzas, A.; Retourne, C.; Jacquet, J. P.; Lavielle, G. Tetrahedron 1978, 34, 3001-3004. (p) Szabó, L.; Sápi, J.; Nógrádi, K.; Kalaus, G.; Szántay, C. Ibid. 1983, 39, 3749-3753.
68. Apovincaminic acid esters: (q) Lörincz, C.; Szász, K.; Kisfaludy, L. Arzneim.-Forsch. (Drug Res.) 1976, 26, 1907. (r) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257-267. (s) Danieli, B.; Lesma, G.; Palmisano, G. Tetrahedron Lett. 1981, 22, 1827-1828, (t) Christie, B. D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239-1246.
69. Apovincaminic acid esters: (q) Lörincz, C.; Szász, K.; Kisfaludy, L. Arzneim.-Forsch. (Drug Res.) 1976, 26, 1907. (r) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257-267. (s) Danieli, B.; Lesma, G.; Palmisano, G. Tetrahedron Lett. 1981, 22, 1827-1828, (t) Christie, B. D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239-1246.
70. Apovincaminic acid esters: (q) Lörincz, C.; Szász, K.; Kisfaludy, L. Arzneim.-Forsch. (Drug Res.) 1976, 26, 1907. (r) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257-267. (s) Danieli, B.; Lesma, G.; Palmisano, G. Tetrahedron Lett. 1981, 22, 1827-1828, (t) Christie, B. D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239-1246.
71. Apovincaminic acid esters: (q) Lörincz, C.; Szász, K.; Kisfaludy, L. Arzneim.-Forsch. (Drug Res.) 1976, 26, 1907. (r) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257-267. (s) Danieli, B.; Lesma, G.; Palmisano, G. Tetrahedron Lett. 1981, 22, 1827-1828, (t) Christie, B. D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239-1246.
72. For a preliminary account of this work see: Mekouar, K.; Ambroise, L.; Desmaële, D.; d'Angelo, J. Synlett, Special Issue May 1995, 529-532.
73. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. d'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends in Organic Synthesis; Pandalai, S. G., Ed.; Trivandrum: India, 1993; Vol. 4, pp 555-615.
74. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. d'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends in Organic Synthesis; Pandalai, S. G., Ed.; Trivandrum: India, 1993; Vol. 4, pp 555-615.
75. Ambroise, L.; Chassagnard, C.; Revial, G.; d'Angelo, J. Tetrahedron: Asymmetry 1991, 2, 407-410.
76. Sugasawa, S.; Fujii, T. Pharm. Bull. (Japan) 1955, 3, 47-52. Ban, Y. Ibid. 1955, 3, 53-59. Barash, M.; Osbond, J. M.; Wickens, J. C. J. Chem. Soc. 1959, 3530-3543.
77. Sugasawa, S.; Fujii, T. Pharm. Bull. (Japan) 1955, 3, 47-52. Ban, Y. Ibid. 1955, 3, 53-59. Barash, M.; Osbond, J. M.; Wickens, J. C. J. Chem. Soc. 1959, 3530-3543.
78. Sugasawa, S.; Fujii, T. Pharm. Bull. (Japan) 1955, 3, 47-52. Ban, Y. Ibid. 1955, 3, 53-59. Barash, M.; Osbond, J. M.; Wickens, J. C. J. Chem. Soc. 1959, 3530-3543.
79. Ambroise, L.; Desmaële, D.; Mahuteau, J.; d'Angelo, J. Tetrahedron Lett. 1994, 35, 9705-9708.
80. Barton, D. H. R.; Me Combie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585. Hartwig, W. Tetrahedron 1983, 39, 2609-2645.
81. Barton, D. H. R.; Me Combie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585. Hartwig, W. Tetrahedron 1983, 39, 2609-2645.
82. Unexpectedly, compound 17 (6%) was also isolated in this reaction, along with unidentified indolic derivatives.
83. Kabalka, G. W.; Baker, J. D., Jr. J. Org. Chem. 1975, 40, 1834-1835.
84. Caglioti, L.; Grasselli, P.; Selva, A. Gazz. Chim. Ital. 1964, 537-551.
85. 2.