Tributyltin hydride induced intramolecular aryl radical cyclizations: Synthesis of biologically interesting organic compounds

Current Organic Chemistry

Volumn 3, Issue 5, 1999, Pages 469-496

  Banik, Bimal K ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; INSECTICIDES; ORGANIC COMPOUNDS;

ALKYL RADICALS; ANTITUMOUR AGENTS; ARYL RADICAL CYCLIZATION; LARGE RINGS; RADICAL CYCLIZATIONS; RING SYSTEMS; SMALL RING SYSTEMS; TERPENOIDS; TRIBUTYLTIN HYDRIDE;

HYDRIDES;

ALKALOID; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; ORGANIC COMPOUND; RADICAL; TERPENOID; TRIBUTYLTIN;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 0032794717     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

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96. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
97. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
98. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
99. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
100. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
101. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
102. The starting ketones were prepared by conjugate addition reaction. For example, see: (a) Banik, B. K.; Chakraborti, A. K., Ghatak, U. R. J. Chem. Res.(S), 1986, 406; J. Chem. Res. (M), 1986, 3391. (b) Banik, B. K., Ghosh, S., Ghatak, U. R. Tetrahedron, 1988, 44, 6947. (c) Banik, B. K.; Ghatak, U. R. Synth. Commun., 1989, 19, 1351. (d) Ghosh, S.; Banik, B. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans 1, 1991, 3189. The starting ketoesters were prepared by conjugate addition of cyanide, hydrolysis of the cyanide and esterification reaction. For example, see: (a) Ghatak, U. R.; Chakravorty, S. J. Org. Chem., 1976, 41, 1089. (b) Banik, B. K.; Ghatak, U. R. Tetrahedron, 1989, 45, 3547.
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138. Beckwith et al. studied the mechanism of radical mediated cyclization reactions extensively. For some references see: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Austral. J. Chem., 1972, 25, 1081. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun., 1974, 472. (c) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc., 1974, 96, 1613. (d) Beckwith, A. L.J.; Gara, W. B. J. Chem. Soc., Perkin Trans 2, 1975, 593. (e) Beckwith, L. J.; Schiesser, C. H. Tetrahedron Lett., 1985, 26, 373. (f) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674. (g) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
139. Beckwith et al. studied the mechanism of radical mediated cyclization reactions extensively. For some references see: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Austral. J. Chem., 1972, 25, 1081. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun., 1974, 472. (c) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc., 1974, 96, 1613. (d) Beckwith, A. L.J.; Gara, W. B. J. Chem. Soc., Perkin Trans 2, 1975, 593. (e) Beckwith, L. J.; Schiesser, C. H. Tetrahedron Lett., 1985, 26, 373. (f) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674. (g) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
140. Beckwith et al. studied the mechanism of radical mediated cyclization reactions extensively. For some references see: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Austral. J. Chem., 1972, 25, 1081. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun., 1974, 472. (c) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc., 1974, 96, 1613. (d) Beckwith, A. L.J.; Gara, W. B. J. Chem. Soc., Perkin Trans 2, 1975, 593. (e) Beckwith, L. J.; Schiesser, C. H. Tetrahedron Lett., 1985, 26, 373. (f) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674. (g) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
141. Beckwith et al. studied the mechanism of radical mediated cyclization reactions extensively. For some references see: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Austral. J. Chem., 1972, 25, 1081. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun., 1974, 472. (c) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc., 1974, 96, 1613. (d) Beckwith, A. L.J.; Gara, W. B. J. Chem. Soc., Perkin Trans 2, 1975, 593. (e) Beckwith, L. J.; Schiesser, C. H. Tetrahedron Lett., 1985, 26, 373. (f) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674. (g) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
142. Beckwith et al. studied the mechanism of radical mediated cyclization reactions extensively. For some references see: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Austral. J. Chem., 1972, 25, 1081. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun., 1974, 472. (c) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc., 1974, 96, 1613. (d) Beckwith, A. L.J.; Gara, W. B. J. Chem. Soc., Perkin Trans 2, 1975, 593. (e) Beckwith, L. J.; Schiesser, C. H. Tetrahedron Lett., 1985, 26, 373. (f) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674. (g) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
143. Beckwith et al. studied the mechanism of radical mediated cyclization reactions extensively. For some references see: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Austral. J. Chem., 1972, 25, 1081. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun., 1974, 472. (c) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc., 1974, 96, 1613. (d) Beckwith, A. L.J.; Gara, W. B. J. Chem. Soc., Perkin Trans 2, 1975, 593. (e) Beckwith, L. J.; Schiesser, C. H. Tetrahedron Lett., 1985, 26, 373. (f) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc., 1989, 111, 2674. (g) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
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159. While preparing the manuscript for the final submission, two important papers appeared in the literature based on this subject, see: (a) Cossy, J.; Tresnard, L.; Pardo, D. G. Tetrahedron Lett., 1999, 40, 1125. (b) Ishibashi, H.; Inomata, M.; Ohba, M. Tetrahedron Lett., 1999, 40, 1149.