Enantioselective Total Synthesis of (+)-Azimine and (+)-Carpaine

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3839-3842

  Sato, Taro ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 BUTANETRIOL; ACID; ALKALOID; AZIMIC ACID; AZIMINE; BUTANE; CARPAINE; CARPAMIC ACID; LACTONE; NITROSO DERIVATIVE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DIELS ALDER REACTION; DILACTONIZATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; MEDICINAL PLANT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0242543832     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030088w     Document Type: Article

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11. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
12. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
13. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
14. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
15. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
16. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
17. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
18. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
19. For the synthesis of racemic azimic acid, see: (a) Brown, E.; Dhal, R. Tetrhaedron Lett. 1974, 1029-1032. (b) Brown, E.; Dhal, R. J. Chem. Soc., Perkin Trans. 1 1976, 2190-2193. (c) Natsume, M.; Ogawa, M. Heterocycles 1980, 14, 169-173. (d) Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. For the synthesis of (+)-azimic acid, see: (e) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394. (f) Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. (g) Kiguchi, T.; Shirakawa, M.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1996, 44, 1282-1284. (h) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606. (i) Kumar, K. K.; Datta, A. Tetrahedron 1999, 55, 13899-13906. (j) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963-3965.
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