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Volumn , Issue 26, 2007, Pages 4320-4327

Synthesis of a 3-arylisoquinoline alkaloid, decumbenine B

Author keywords

Cyclization; Decumbenine B; Heck reaction; Isoquinoline alkaloid; Nitrogen heterocycles

Indexed keywords


EID: 34548806487     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700225     Document Type: Article
Times cited : (41)

References (95)
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    • For the isolation of other 3-arylisoquinoline alkaloids, corydalic acid methyl ester and corydamine, see: a
    • For the isolation of other 3-arylisoquinoline alkaloids, corydalic acid methyl ester and corydamine, see: a) G. Nonaka, Y. Kodera, I. Nishioka, Chem. Pharm. Bull. 1973, 21, 1020-1026;
    • (1973) Chem. Pharm. Bull , vol.21 , pp. 1020-1026
    • Nonaka, G.1    Kodera, Y.2    Nishioka, I.3
  • 11
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    • For the biosynthesis of 3-arylisoquinolines, see
    • For the biosynthesis of 3-arylisoquinolines, see: A. Yagi, G. Nonaka, S. Nakayama, I. Nishioka, Phytochemistry 1977, 16, 1197-1199.
    • (1977) Phytochemistry , vol.16 , pp. 1197-1199
    • Yagi, A.1    Nonaka, G.2    Nakayama, S.3    Nishioka, I.4
  • 18
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    • Selected articles for the preparation of 3-arylisoquinoline derivatives: by Bischler-Napieralski reaction: a E. Domínguez, E. Lete, Heterocycles 1983, 20, 1247-1251;
    • Selected articles for the preparation of 3-arylisoquinoline derivatives: by Bischler-Napieralski reaction: a) E. Domínguez, E. Lete, Heterocycles 1983, 20, 1247-1251;
  • 25
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    • by Pictet-Spengler reaction: h S. F. Dyke, D. W. Browm, M. Sainsbury, G. Hardy, Tetrahedron 1971, 27, 3495-3502;
    • by Pictet-Spengler reaction: h) S. F. Dyke, D. W. Browm, M. Sainsbury, G. Hardy, Tetrahedron 1971, 27, 3495-3502;
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    • by transformation of protoberberines: q M. Hanaoka, T. Motonishi, C. Mukai, J. Chem. Soc. Chem. Commun. 1984, 718-719;
    • by transformation of protoberberines: q) M. Hanaoka, T. Motonishi, C. Mukai, J. Chem. Soc. Chem. Commun. 1984, 718-719;
  • 37
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    • by an anionic cyclization: t R. D. Clark, A. Jahangir, J. Org. Chem. 1989, 54, 1174-1178;
    • by an anionic cyclization: t) R. D. Clark, A. Jahangir, J. Org. Chem. 1989, 54, 1174-1178;
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    • by other methods: w A. Carty, I. W. Elliott, G. M. Lenior, Can. J. Chem. 1984, 2435-2439;
    • by other methods: w) A. Carty, I. W. Elliott, G. M. Lenior, Can. J. Chem. 1984, 2435-2439;
  • 53
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    • For other methods for the preparation of dibenz[b,f]indolizines, see: a G. Wittig, H. Tenhaeff, W. Schoch, G. Koenig, Justus Liebigs Ann. Chem. 1951, 572, 1-22;
    • For other methods for the preparation of dibenz[b,f]indolizines, see: a) G. Wittig, H. Tenhaeff, W. Schoch, G. Koenig, Justus Liebigs Ann. Chem. 1951, 572, 1-22;
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    • A similar N-acylation with 2-bromophenylacetyl chloride was unsuccessful. The reaction with 3-(2-bromophenyl)propanoyl chloride afforded 2-[3-(2-bromophenyl)propanoyl]-1,2-dihydroisoquinoline almost quantitatively, which underwent neither a Heck cyclization nor a radical cyclization.
    • A similar N-acylation with 2-bromophenylacetyl chloride was unsuccessful. The reaction with 3-(2-bromophenyl)propanoyl chloride afforded 2-[3-(2-bromophenyl)propanoyl]-1,2-dihydroisoquinoline almost quantitatively, which underwent neither a Heck cyclization nor a radical cyclization.
  • 89
    • 0842304432 scopus 로고    scopus 로고
    • 6-Bromo-2,3-(methylenedioxy)benzoic acid was prepared by the carboxylation of 3,4-(methylenedioxy)phenylbromide (72% yield) according to: a) P. A. Plé, T. P. Green, L. F. Hennequin, J. Curwen, M. Fennell, J. Allen, C. L. Brempt, G. Costello, J. Med. Chem. 2004, 47, 871-887,
    • 6-Bromo-2,3-(methylenedioxy)benzoic acid was prepared by the carboxylation of 3,4-(methylenedioxy)phenylbromide (72% yield) according to: a) P. A. Plé, T. P. Green, L. F. Hennequin, J. Curwen, M. Fennell, J. Allen, C. L. Brempt, G. Costello, J. Med. Chem. 2004, 47, 871-887,
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    • and also by the bromination of 2,3-(methylenedioxy)benzoic acid with DBDMH (62% yield, by a modification of the method reported for a dimethoxy derivative) according to: b) J. Auerbach, S. A. Weissman, T. J. Blacklock, M. R. Angeles, K. Hoogsteen, Tetrahedron Lett. 1993, 34, 931-934;
    • and also by the bromination of 2,3-(methylenedioxy)benzoic acid with DBDMH (62% yield, by a modification of the method reported for a dimethoxy derivative) according to: b) J. Auerbach, S. A. Weissman, T. J. Blacklock, M. R. Angeles, K. Hoogsteen, Tetrahedron Lett. 1993, 34, 931-934;
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    • [11d]
    • [11d]
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    • For the autooxidation of dihydroisoquinolines, see
    • For the autooxidation of dihydroisoquinolines, see: N. Sotomayor, E. Domíngues, E. Lete, Tetrahedron 1995, 51, 12721-12730.
    • (1995) Tetrahedron , vol.51 , pp. 12721-12730
    • Sotomayor, N.1    Domíngues, E.2    Lete, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.