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Volumn 44, Issue 50, 2003, Pages 9057-9060

Lewis acid-promoted tandem desulfurization and hydroxylation of γ-phenylthio-substituted lactams: Novel synthetic strategy of isoindolobenzazepine alkaloid, chilenine

Author keywords

[No Author keywords available]

Indexed keywords

CHILENINE; COPPER DERIVATIVE; ISOINDOLE DERIVATIVE; LACTAM DERIVATIVE; LEWIS ACID; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242626809     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.204     Document Type: Article
Times cited : (23)

References (28)
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    • (a) Weinstock, J.; Hieble, J. P.; Wilson, J. W. Drugs Future 1985, 10, 645-651; (b) Csende, F.; Szabo, Z.; Stajer, G. Heterocycles 1993, 36, 1809-1821; (c) Epsztajn, J.; Grzebak, R.; Jozwiak, A. Synthesis 1996, 1212-1216; (d) Marchalin, S.; Decroix, B. Heterocycles 1995, 41, 689-696; (e) Daich, A.; Marchalin, S.; Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 9187-9190 and recent synthetic examples, see: (f) Yoda, H.; Nakahama, A.; Koketsu, T.; Takabe, K. Tetrahedron Lett. 2002, 43, 4667-4669; (g) Padwa, A.; Beall, L. S.; Eidell, C. K.; Worsencroft, K. J. J. Org. Chem. 2001, 66, 2414-2421; (h) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3923-3925; (i) Couture, A.; Deniau, E.; Grandclaudon, P.; Hoarau, C. Tetrahedron 2000, 56, 1491-1499; (j) Ruchirawat, S.; Sahakitpichan, P. Tetrahedron Lett. 2000, 41, 8007-8010; (k) Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169-2172; (l) Rodríguez, G.; Castedo, L.; Domínguez, D.; Saá, C. Tetrahedron Lett. 1998, 39, 6551-6554; (m) Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817-821; (n) Rodríguez, G.; Cid, M. M.; Saá, C. Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780-2782 and references cited therein.
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    • 1H NMR). It is not clear at present which effect (stereoelectronic or steric effect) would be more predominant on this regioselectivity
    • 1H NMR). It is not clear at present which effect (stereoelectronic or steric effect) would be more predominant on this regioselectivity.


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