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Volumn 72, Issue 13, 2007, Pages 4886-4891

Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; AZIRIDINE; IMINES;

EID: 34250852857     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070668x     Document Type: Article
Times cited : (81)

References (44)
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  • 18
    • 33749327279 scopus 로고    scopus 로고
    • For representative recent examples, see: a
    • For representative recent examples, see: (a) Fürstner, A.; Kennedy, J. W. J. Chem. Eur. J. 2006, 12, 7398-7410.
    • (2006) Chem. Eur. J , vol.12 , pp. 7398-7410
    • Fürstner, A.1    Kennedy, J.W.J.2
  • 25
    • 0027974072 scopus 로고
    • For, a previous application of intramolecular 1,3-dipolar cycloaddition in synthesis of phenanthroindolizidine alkaloids, see
    • For, a previous application of intramolecular 1,3-dipolar cycloaddition in synthesis of phenanthroindolizidine alkaloids, see: Pearson, W. H.; Walavalkar, R. Tetrahedron 1994, 50, 12293-12304.
    • (1994) Tetrahedron , vol.50 , pp. 12293-12304
    • Pearson, W.H.1    Walavalkar, R.2
  • 28
    • 0037185504 scopus 로고    scopus 로고
    • The spontaneous oxidation of the C-H bond flanked between an imine and an aromatic ring has been observed by others, see: (a) Andreu, I, Cabedo, N, Atassi, G, Pierre, A, Caignard, D. H, Renard, P, Cortes, D, Bermejo, A. Tetrahedron Lett. 2002, 43, 757-759
    • The spontaneous oxidation of the C-H bond flanked between an imine and an aromatic ring has been observed by others, see: (a) Andreu, I.; Cabedo, N.; Atassi, G.; Pierre, A.; Caignard, D. H.; Renard, P.; Cortes, D.; Bermejo, A. Tetrahedron Lett. 2002, 43, 757-759.
  • 35
    • 0002899589 scopus 로고
    • Curran, D. P, Ed, JAI Press: Greenwich, CT
    • (a) Padwa, A.; Schoffstall, A. M. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 1-89.
    • (1990) Advances in Cycloaddition , vol.2 , pp. 1-89
    • Padwa, A.1    Schoffstall, A.M.2
  • 36
    • 0000629986 scopus 로고
    • Intermolecular 1,3-Dipolar Cycloadditions
    • Trost, B. M, Fleming, I, Eds, Pergamon: London
    • (b) Padwa, A. Intermolecular 1,3-Dipolar Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 4, pp 1069-1109.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069-1109
    • Padwa, A.1
  • 37
    • 0000629986 scopus 로고
    • Intramolecular 1,3-Dipolar Cycloadditions: Azomethine Imine Cyclizations
    • Trost, B. M, Fleming, I, Eds, Pergamon: London
    • (c) Wade, P. A. Intramolecular 1,3-Dipolar Cycloadditions: Azomethine Imine Cyclizations. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 4, pp 1111-1168.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1111-1168
    • Wade, P.A.1
  • 39
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    • For recent reviews, see: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140.
    • (2004) Tetrahedron , vol.60 , pp. 7117-7140
    • Grubbs, R.H.1
  • 41
    • 34250826564 scopus 로고    scopus 로고
    • The azidophosphonium salt 17 was prepared as described in ref 12, and see also: Chhen, A. I.; Soufiaoui, M.; Carrié, R. Bull. Soc. Chim. Fr. 1992, 129, 308-314.
    • The azidophosphonium salt 17 was prepared as described in ref 12, and see also: Chhen, A. I.; Soufiaoui, M.; Carrié, R. Bull. Soc. Chim. Fr. 1992, 129, 308-314.
  • 42
    • 34250850825 scopus 로고    scopus 로고
    • For the construction of the seven-membered ring (azepine) analogue, we prepared the two-carbon homologated azidoalkene, 10-(7-azidohept-1-enyl)-2,3,6- trimethoxyphenanthrene, as a mixture of Z/E isomers (4:1). Unfortunately, heating the two-carbon homologated azidoalkene at 135°C in a sealed tube did not provide any noticeable cyclized product, and increasing the temperature higher than 200°C resulted only in unreacted starting material and decomposed material.
    • For the construction of the seven-membered ring (azepine) analogue, we prepared the two-carbon homologated azidoalkene, 10-(7-azidohept-1-enyl)-2,3,6- trimethoxyphenanthrene, as a mixture of Z/E isomers (4:1). Unfortunately, heating the two-carbon homologated azidoalkene at 135°C in a sealed tube did not provide any noticeable cyclized product, and increasing the temperature higher than 200°C resulted only in unreacted starting material and decomposed material.


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