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Volumn 77, Issue 23, 2012, Pages 10773-10781

A raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

REDUCTIVE CYCLIZATION;

EID: 84870874016     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302132d     Document Type: Article
Times cited : (30)

References (27)
  • 6
    • 84869179673 scopus 로고    scopus 로고
    • For the application of related protocols to total syntheses of the Aspidosperma alkaloids limaspermidine and 1-acetylaspidoalbidine, see: 10.1021/ol3026846
    • For the application of related protocols to total syntheses of the Aspidosperma alkaloids limaspermidine and 1-acetylaspidoalbidine, see: Tan, S. H.; Banwell, M. G.; Willis, A. C.; Reekie, T. A. Org. Lett. 2012, 10.1021/ol3026846
    • (2012) Org. Lett.
    • Tan, S.H.1    Banwell, M.G.2    Willis, A.C.3    Reekie, T.A.4
  • 13
    • 56449130065 scopus 로고    scopus 로고
    • Nitrile 9 has been obtained previously via an organo-catalyzed Dielsa-Alder reaction between N-phenylmaleimide and 3-vinylindole, and its acquisition constitutes a formal total synthesis of the racemic modification of the Strychnos alkaloid tubifolidine
    • Nitrile 9 has been obtained previously via an organo-catalyzed Dielsa-Alder reaction between N-phenylmaleimide and 3-vinylindole, and its acquisition constitutes a formal total synthesis of the racemic modification of the Strychnos alkaloid tubifolidine: Gioia, C.; Hauville, A.; Bernardi, L.; Fini, F.; Ricci, A. Angew. Chem., Int. Ed. 2008, 47, 9236
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 9236
    • Gioia, C.1    Hauville, A.2    Bernardi, L.3    Fini, F.4    Ricci, A.5
  • 14
    • 0009464699 scopus 로고
    • 4-mediated reduction of 20-deethyl-4-demethyldasycarpidine
    • 4-mediated reduction of 20-deethyl-4-demethyldasycarpidine: Bosch, J.; Amat, M.; Sanfeliu, E.; Miranda, M. A. Tetrahedron 1985, 41, 2557
    • (1985) Tetrahedron , vol.41 , pp. 2557
    • Bosch, J.1    Amat, M.2    Sanfeliu, E.3    Miranda, M.A.4
  • 15
    • 0023940683 scopus 로고
    • Bosch and co-workers have reported a nine-step synthesis of compound 11 from N-benzylpiperidin-4-one
    • Bosch and co-workers have reported a nine-step synthesis of compound 11 from N-benzylpiperidin-4-one: Bonjoch, J.; Quirante, J.; Rodriguez, M.; Bosch, J. Tetrahedron 1988, 44, 2087
    • (1988) Tetrahedron , vol.44 , pp. 2087
    • Bonjoch, J.1    Quirante, J.2    Rodriguez, M.3    Bosch, J.4
  • 16
    • 0000221935 scopus 로고    scopus 로고
    • These conditions are similar to those employed by Shibasaki and co-workers in a closely related conversion
    • These conditions are similar to those employed by Shibasaki and co-workers in a closely related conversion: Shimizu, S.; Ohori, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547
    • (1998) J. Org. Chem. , vol.63 , pp. 7547
    • Shimizu, S.1    Ohori, K.2    Arai, T.3    Sasai, H.4    Shibasaki, M.5
  • 17
    • 0032575166 scopus 로고    scopus 로고
    • For a distinctly different route to such frameworks carrying a substituent at this position, see
    • For a distinctly different route to such frameworks carrying a substituent at this position, see: Shin, K.; Moriya, M.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 3765
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3765
    • Shin, K.1    Moriya, M.2    Ogasawara, K.3
  • 18
    • 84870932376 scopus 로고    scopus 로고
    • CCDC 900779 contains the supplementary crystallographic data for compound 18. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via.
    • CCDC 900779 contains the supplementary crystallographic data for compound 18. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.