An aza-achmatowicz approach toward the hydroxylated piperidine alkaloids (±)-azimic acid and (±)-deoxocassine

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4029-4031

  Cassidy, Michael P ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HYDROXYLATION; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

ALKALOIDS; AZA COMPOUNDS; HYDROXYLATION; MODELS, CHEMICAL; OXIDATION-REDUCTION; PIPERIDINES;

EID: 8744231829     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048326q     Document Type: Article

References (49)

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19. For the synthesis of azimic acid, see: (a) Brown, E.; Dhal, R. Tetrahedron Lett. 1974, 1029. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169. (d) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391. (e) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659. (f) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282. (g) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589. (h) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899.
20. For the synthesis of azimic acid, see: (a) Brown, E.; Dhal, R. Tetrahedron Lett. 1974, 1029. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169. (d) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391. (e) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659. (f) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282. (g) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589. (h) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899.
21. For the synthesis of azimic acid, see: (a) Brown, E.; Dhal, R. Tetrahedron Lett. 1974, 1029. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169. (d) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391. (e) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659. (f) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282. (g) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589. (h) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899.
22. For the synthesis of azimic acid, see: (a) Brown, E.; Dhal, R. Tetrahedron Lett. 1974, 1029. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169. (d) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391. (e) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659. (f) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282. (g) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589. (h) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899.
23. For the synthesis of carpamic acid, see: (a) Brown, E.; Bourgouin, A. Chem. Lett. 1974, 109. (b) Brown, E.; Bourgouin, A. Tetrahedron 1975, 31, 1047. (c) Holmes, A. B.; Swithenbank, C.; Williams, S. F. Chem. Commun. 1986, 265. (d) Singh, R.; Ghosh, S. K. Tetrahedron Lett. 2002, 43, 7711.
24. For the synthesis of carpamic acid, see: (a) Brown, E.; Bourgouin, A. Chem. Lett. 1974, 109. (b) Brown, E.; Bourgouin, A. Tetrahedron 1975, 31, 1047. (c) Holmes, A. B.; Swithenbank, C.; Williams, S. F. Chem. Commun. 1986, 265. (d) Singh, R.; Ghosh, S. K. Tetrahedron Lett. 2002, 43, 7711.
25. For the synthesis of carpamic acid, see: (a) Brown, E.; Bourgouin, A. Chem. Lett. 1974, 109. (b) Brown, E.; Bourgouin, A. Tetrahedron 1975, 31, 1047. (c) Holmes, A. B.; Swithenbank, C.; Williams, S. F. Chem. Commun. 1986, 265. (d) Singh, R.; Ghosh, S. K. Tetrahedron Lett. 2002, 43, 7711.
26. For the synthesis of carpamic acid, see: (a) Brown, E.; Bourgouin, A. Chem. Lett. 1974, 109. (b) Brown, E.; Bourgouin, A. Tetrahedron 1975, 31, 1047. (c) Holmes, A. B.; Swithenbank, C.; Williams, S. F. Chem. Commun. 1986, 265. (d) Singh, R.; Ghosh, S. K. Tetrahedron Lett. 2002, 43, 7711.
27. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
28. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
29. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
30. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
31. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
32. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
33. For the synthesis of other hydroxylated piperidine alkaloids, see: (a) Cossy, J.; Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002, 67, 1982. (b) Dransfield, P. J.; Gore, P. M.; Shipman, M.; Slawin, A. M. Z. J. Chem. Soc., Chem. Commun. 2002, 150. (c) Jourdant, A.; Zhu, J. Tetrahedron Lett. 2001, 42, 3431. (d) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829. (e) Zhou, W.-S.; Lu, Z.-H. Tetrahedron 1993, 49, 4659. (f) Cook, G. R.; Beholz, L. G.; Stille, J. R.; J. Org. Chem. 1994, 59, 3575. (g) Zhou, W.-S.; Liao, L.-X.; Xu, Y.-M.; Yang, C.-F. Tetrahedron Lett. 1998, 39, 9227. (h) Datta, A.; Kumar, K. K. Tetrahedron 1999, 55. 13899. (i) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
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