Mn(III)/Cu(II)-mediated oxidative radical cyclization of α-(methylthio)acetamides leading to erythrinanes

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 312-318

  Chikaoka, Shiho ^a   Toyao, Atsushi ^a   Ogasawara, Mizuho ^a   Tamura, Osamu ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL CYCLIZATION;

COPPER; MANGANESE; OXIDATION; POSITIVE IONS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

3 DEMETHOXYERYTHRATIDINONE; ACETAMIDE DERIVATIVE; ALKALOID; ALPHA (METHYLTHIO)ACETAMIDE; COPPER DERIVATIVE; ERYTHRINANE; MANGANESE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACETAMIDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ERYTHRINA; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MANGANESE; OXIDATION-REDUCTION; PLANTS, MEDICINAL;

EID: 0037462393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020573p     Document Type: Article

References (33)

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19. 3, see: Méou, A.; Lamarque, L.; Brun, P. Tetrahedron Lett. 2002, 43, 5301. Garzino, F.; Méou, A.; Brun, P. Tetrahedron Lett. 2002, 43, 5049. Bar, G.; Parsons, A. F.; Thomas, C. B. Synlett 2002, 1069. Hirase, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2002, 67, 970. Taylor, E. C.; Liu, B. J. Org. Chem. 2001, 66, 3726. Lavilla, R.; Spada, A.; Carranco, I.; Bosch, J. J. Org. Chem. 2001, 66, 1487. Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Zanardi, G. Tetrahedron 2001, 57, 7221. Yang, D.; Xu, M. Org. Lett. 2001, 3, 1785. Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658. D'Annibale, A.; Nanni, D.; Trogolo, C.; Umani, F. Org. Lett. 2000, 2, 401. Davies, D. T.; Kapur, N.; Parsons, A. F. Tetrahedron 2000, 56, 3941. Wu, Y.-L.; Chuang, C.-P.; Lin, P.-Y. Tetrahedron 2000, 56, 6209. Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. Chuang, C.-P.; Wang, S.-F. Tetrahedron 1998, 54, 10043. Chowdhury, F. A.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1998, 39, 7931. See also references therein.
20. 3, see: Méou, A.; Lamarque, L.; Brun, P. Tetrahedron Lett. 2002, 43, 5301. Garzino, F.; Méou, A.; Brun, P. Tetrahedron Lett. 2002, 43, 5049. Bar, G.; Parsons, A. F.; Thomas, C. B. Synlett 2002, 1069. Hirase, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2002, 67, 970. Taylor, E. C.; Liu, B. J. Org. Chem. 2001, 66, 3726. Lavilla, R.; Spada, A.; Carranco, I.; Bosch, J. J. Org. Chem. 2001, 66, 1487. Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Zanardi, G. Tetrahedron 2001, 57, 7221. Yang, D.; Xu, M. Org. Lett. 2001, 3, 1785. Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658. D'Annibale, A.; Nanni, D.; Trogolo, C.; Umani, F. Org. Lett. 2000, 2, 401. Davies, D. T.; Kapur, N.; Parsons, A. F. Tetrahedron 2000, 56, 3941. Wu, Y.-L.; Chuang, C.-P.; Lin, P.-Y. Tetrahedron 2000, 56, 6209. Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229. Chuang, C.-P.; Wang, S.-F. Tetrahedron 1998, 54, 10043. Chowdhury, F. A.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1998, 39, 7931. See also references therein.
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