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Volumn 124, Issue 42, 2002, Pages 12416-12417

Synthesis of (-)-morphine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MORPHINE; NATURAL PRODUCT; OPIATE;

EID: 0037164053     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027882h     Document Type: Article
Times cited : (109)

References (40)
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    • For leading references to previous syntheses of enantiomerically pure morphine, see: (a) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028. (b) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250. (c) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908. (d) Nagata, H.; Miyazawa, N.; Ogasawara, K. Chem. Commun. 2001, 1094.
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    • For leading references to previous syntheses of enantiomerically pure morphine, see: (a) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028. (b) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250. (c) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908. (d) Nagata, H.; Miyazawa, N.; Ogasawara, K. Chem. Commun. 2001, 1094.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • Kametani, T.1    Ihara, M.2    Fukumoto, K.3    Yagi, H.4
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous syntheses of racemic morphine, see: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312. (c) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550. (d) Morrison, G. C.; Waite, R. O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 41, 4055. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239. (g) Lie, T. S.; Maat, L.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas 1979, 98, 419. (h) Rice, K. C. J. Org. Chem. 1980, 45, 3135. (i) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285. (j) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227. (k) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473. (l) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959. (m) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
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    • For leading references to previous approaches to the ring system of morphine, see: (a) Monkivic, I.; Conway, T. T.; Wong, H.; Perron, Y. G.; Patchter, I. J.; Belleau, B. J. Am. Chem. Soc. 1973, 95, 7910. (b) Schultz, A. G.; Lucci, R. D. J. Chem. Soc., Chem. Commun. 1976, 925. (c) Ciganek, E. J. Am. Chem. Soc. 1981, 103, 6261. (d) Boger, D. L.; Patel, M.; Mullican, M. D. Tetrahedron Lett. 1982, 23, 4559. (e) Hudlicky, T.; Boros, C. H.; Boros, E. E. Synthesis 1992, 174.
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    • For leading references to previous approaches to the ring system of morphine, see: (a) Monkivic, I.; Conway, T. T.; Wong, H.; Perron, Y. G.; Patchter, I. J.; Belleau, B. J. Am. Chem. Soc. 1973, 95, 7910. (b) Schultz, A. G.; Lucci, R. D. J. Chem. Soc., Chem. Commun. 1976, 925. (c) Ciganek, E. J. Am. Chem. Soc. 1981, 103, 6261. (d) Boger, D. L.; Patel, M.; Mullican, M. D. Tetrahedron Lett. 1982, 23, 4559. (e) Hudlicky, T.; Boros, C. H.; Boros, E. E. Synthesis 1992, 174.
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    • For leading references to previous approaches to the ring system of morphine, see: (a) Monkivic, I.; Conway, T. T.; Wong, H.; Perron, Y. G.; Patchter, I. J.; Belleau, B. J. Am. Chem. Soc. 1973, 95, 7910. (b) Schultz, A. G.; Lucci, R. D. J. Chem. Soc., Chem. Commun. 1976, 925. (c) Ciganek, E. J. Am. Chem. Soc. 1981, 103, 6261. (d) Boger, D. L.; Patel, M.; Mullican, M. D. Tetrahedron Lett. 1982, 23, 4559. (e) Hudlicky, T.; Boros, C. H.; Boros, E. E. Synthesis 1992, 174.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 4559
    • Boger, D.L.1    Patel, M.2    Mullican, M.D.3
  • 27
    • 0026587908 scopus 로고
    • For leading references to previous approaches to the ring system of morphine, see: (a) Monkivic, I.; Conway, T. T.; Wong, H.; Perron, Y. G.; Patchter, I. J.; Belleau, B. J. Am. Chem. Soc. 1973, 95, 7910. (b) Schultz, A. G.; Lucci, R. D. J. Chem. Soc., Chem. Commun. 1976, 925. (c) Ciganek, E. J. Am. Chem. Soc. 1981, 103, 6261. (d) Boger, D. L.; Patel, M.; Mullican, M. D. Tetrahedron Lett. 1982, 23, 4559. (e) Hudlicky, T.; Boros, C. H.; Boros, E. E. Synthesis 1992, 174.
    • (1992) Synthesis , pp. 174
    • Hudlicky, T.1    Boros, C.H.2    Boros, E.E.3
  • 33
    • 0010968685 scopus 로고    scopus 로고
    • note
    • 13C NMR and also to simplify the chiral ketal product distribution and separation.
  • 35
    • 0010963407 scopus 로고    scopus 로고
    • note
    • (b) Sodium bis(2-methoxyethoxy)aluminum hydride is sold as both Red-Al and Vitride.
  • 37
    • 0011011089 scopus 로고    scopus 로고
    • note
    • Attempted epoxidation with peracids led to extensive decomposition.
  • 40
    • 0011005339 scopus 로고    scopus 로고
    • note
    • β-Tetralone 13 was initially ketalized with (R,R)-(+)-hydrobenzoin. The first ketal diastereomer to elute via chromatography was converted to the p-bromobenzenesulfonamide i. This was determined by X-ray analysis to have the configuration at C-9, C-13, and C-14 shown.


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