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Volumn 71, Issue 4, 2006, Pages 1746-1749

Regioselective 6-endo cyclizations of 2-indolylacyl radicals: Total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; ETRAHYDROPYRIDINE;

EID: 33644556461     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052428s     Document Type: Article
Times cited : (38)

References (43)
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    • (b) Joule, J. A. Indoles, The Monoterpenoid Indole Alkaloids. In The Chemistry of Heterocyclic Compounds; Saxton, J. E., Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1983; Part 4, pp 275-286.
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    • Joule, J.A.1
  • 3
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    • Brosi, A., Ed.; Academic Press: New York
    • (c) Gribble, G. W. The Alkaloids; Brosi, A., Ed.; Academic Press: New York, 1990; Vol. 39, pp 239-352.
    • (1990) The Alkaloids , vol.39 , pp. 239-352
    • Gribble, G.W.1
  • 4
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    • and references therein
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    • Knölker, H.-J.1    Reddy, K.R.2
  • 5
    • 0025143479 scopus 로고
    • For representative syntheses of olivacine since 1990, see: (a) Bäckvall, J.-E.; Plobeck, N. A. J. Org. Chem. 1990, 55, 4528-4531.
    • (1990) J. Org. Chem. , vol.55 , pp. 4528-4531
    • Bäckvall, J.-E.1    Plobeck, N.A.2
  • 13
    • 27444439290 scopus 로고    scopus 로고
    • For the synthesis of ellipticine quinones by intramolecular homolytic acylation of pyridines, see: Bennasar, M.-L.; Roca, T.; Ferrando, F. J. Org. Chem. 2005, 70, 9077-9080.
    • (2005) J. Org. Chem. , vol.70 , pp. 9077-9080
    • Bennasar, M.-L.1    Roca, T.2    Ferrando, F.3
  • 16
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    • Guatambuine was isolated as the (+)-, (-)-, and (±)-forms: (a) Ondetti, M. A.; Deulofeu, V. Tetrahedron 1961, 15, 160-166.
    • (1961) Tetrahedron , vol.15 , pp. 160-166
    • Ondetti, M.A.1    Deulofeu, V.2
  • 18
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    • For previous syntheses of (i)-guatambuine, see: (a) Besselièvre, B.; Husson, H.-P. Tetrahedron 1981, 37, Suppl. No. 1, 241-246.
    • (1981) Tetrahedron , vol.37 , Issue.SUPPL. NO. 1 , pp. 241-246
    • Besselièvre, B.1    Husson, H.-P.2
  • 20
    • 0004269715 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • (a) Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
    • (2001) Radicals in Organic Synthesis
  • 21
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    • (b) Zhang, W. Tetrahedron 2001, 57, 7237-7262.
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    • Zhang, W.1
  • 25
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    • For recent examples of the synthesis of fused azacycles: (a) Miranda, L. D.; Zard, S. Org. Lett. 2002, 4, 1135-1138.
    • (2002) Org. Lett. , vol.4 , pp. 1135-1138
    • Miranda, L.D.1    Zard, S.2
  • 33
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    • For radical cyclizations upon tetrahydropyridines where a carbocycle is created, see: (a) Jenkinson, J. J.; Parsons, P. J.; Eyley, S. C. Synlett 1992, 679-680.
    • (1992) Synlett , pp. 679-680
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  • 41
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    • note
    • We had observed that the indole NH group inhibited the radical cyclization of a related selenoester upon pyridines, probably by interfering at the rearomatization step: see ref 5.
  • 43
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    • note
    • Simple heating of selenoester 9 in 1:1 benzene-acetonitrile for 3 h led to a 3:1 mixture of 9 and 11. In contrast, heating of 9 in benzene for 6 h led to a 10:1 mixture of 9 and 11.


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