메뉴 건너뛰기




Volumn 3, Issue 5, 2005, Pages 836-847

Studies towards the enantioselective synthesis of 5,6,8-trisubstituted amphibian indolizidine alkaloids via enaminone intermediates

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CARBOXYLIC ACIDS; ESTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

EID: 15244338980     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418062c     Document Type: Article
Times cited : (25)

References (42)
  • 3
    • 77957068714 scopus 로고
    • A. Brossi, ed., Academic Press, New York
    • A. S. Howard and J. P. Michael, in The Alkaloids. Chemistry and Pharmacology, A. Brossi, ed., Academic Press, New York, 1986, vol. 28, pp. 183-308; J. P. Michael, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, New York, 2001, vol. 55, pp. 91-258. For annual reports on progress in the chemistry of indolizidine and quinoliridine alkaloids, see:; J. P. Michael, Nat. Prod. Rep., 2004, 21, 625-649 and earlier reviews in this series.
    • (1986) The Alkaloids. Chemistry and Pharmacology , vol.28 , pp. 183-308
    • Howard, A.S.1    Michael, J.P.2
  • 4
    • 0035232404 scopus 로고    scopus 로고
    • G. A. Cordell, ed., Academic Press, New York, For annual reports on progress in the chemistry of indolizidine and quinoliridine alkaloids, see
    • A. S. Howard and J. P. Michael, in The Alkaloids. Chemistry and Pharmacology, A. Brossi, ed., Academic Press, New York, 1986, vol. 28, pp. 183-308; J. P. Michael, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, New York, 2001, vol. 55, pp. 91-258. For annual reports on progress in the chemistry of indolizidine and quinoliridine alkaloids, see:; J. P. Michael, Nat. Prod. Rep., 2004, 21, 625-649 and earlier reviews in this series.
    • (2001) The Alkaloids. Chemistry and Biology , vol.55 , pp. 91-258
    • Michael, J.P.1
  • 5
    • 7744232650 scopus 로고    scopus 로고
    • and earlier reviews in this series
    • A. S. Howard and J. P. Michael, in The Alkaloids. Chemistry and Pharmacology, A. Brossi, ed., Academic Press, New York, 1986, vol. 28, pp. 183-308; J. P. Michael, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, New York, 2001, vol. 55, pp. 91-258. For annual reports on progress in the chemistry of indolizidine and quinoliridine alkaloids, see:; J. P. Michael, Nat. Prod. Rep., 2004, 21, 625-649 and earlier reviews in this series.
    • (2004) Nat. Prod. Rep. , vol.21 , pp. 625-649
    • Michael, J.P.1
  • 6
    • 77956653175 scopus 로고    scopus 로고
    • G. A. Cordell, ed., Academic Press, San Diego
    • J. W. Daly, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, San Diego, 1998, vol. 50, pp. 141-169.; J. W. Daly, T. Kaneko, J. Wilham, H. M. Garraffo, T. F. Spande, A. Espinosa and M. A. Donnelly, Proc. Natl. Acad. Sci. USA, 2002, 99, 13996-14001; J. W. Daly, J. Med. Chem., 2003, 46, 445-452; R. A. Saporito, H. M. Garraffo, M. A. Donnelly, A. L. Edwards, J. T. Longino and J. W. Daly, Proc. Natl. Acad. Sci. USA, 2004, 101, 8045-8050.
    • (1998) The Alkaloids. Chemistry and Biology , vol.50 , pp. 141-169
    • Daly, J.W.1
  • 7
    • 0037195129 scopus 로고    scopus 로고
    • J. W. Daly, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, San Diego, 1998, vol. 50, pp. 141-169.; J. W. Daly, T. Kaneko, J. Wilham, H. M. Garraffo, T. F. Spande, A. Espinosa and M. A. Donnelly, Proc. Natl. Acad. Sci. USA, 2002, 99, 13996-14001; J. W. Daly, J. Med. Chem., 2003, 46, 445-452; R. A. Saporito, H. M. Garraffo, M. A. Donnelly, A. L. Edwards, J. T. Longino and J. W. Daly, Proc. Natl. Acad. Sci. USA, 2004, 101, 8045-8050.
    • (2002) Proc. Natl. Acad. Sci. USA , vol.99 , pp. 13996-14001
    • Daly, J.W.1    Kaneko, T.2    Wilham, J.3    Garraffo, H.M.4    Spande, T.F.5    Espinosa, A.6    Donnelly, M.A.7
  • 8
    • 0037434512 scopus 로고    scopus 로고
    • J. W. Daly, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, San Diego, 1998, vol. 50, pp. 141-169.; J. W. Daly, T. Kaneko, J. Wilham, H. M. Garraffo, T. F. Spande, A. Espinosa and M. A. Donnelly, Proc. Natl. Acad. Sci. USA, 2002, 99, 13996-14001; J. W. Daly, J. Med. Chem., 2003, 46, 445-452; R. A. Saporito, H. M. Garraffo, M. A. Donnelly, A. L. Edwards, J. T. Longino and J. W. Daly, Proc. Natl. Acad. Sci. USA, 2004, 101, 8045-8050.
    • (2003) J. Med. Chem. , vol.46 , pp. 445-452
    • Daly, J.W.1
  • 9
    • 2542626711 scopus 로고    scopus 로고
    • J. W. Daly, in The Alkaloids. Chemistry and Biology, G. A. Cordell, ed., Academic Press, San Diego, 1998, vol. 50, pp. 141-169.; J. W. Daly, T. Kaneko, J. Wilham, H. M. Garraffo, T. F. Spande, A. Espinosa and M. A. Donnelly, Proc. Natl. Acad. Sci. USA, 2002, 99, 13996-14001; J. W. Daly, J. Med. Chem., 2003, 46, 445-452; R. A. Saporito, H. M. Garraffo, M. A. Donnelly, A. L. Edwards, J. T. Longino and J. W. Daly, Proc. Natl. Acad. Sci. USA, 2004, 101, 8045-8050.
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 8045-8050
    • Saporito, R.A.1    Garraffo, H.M.2    Donnelly, M.A.3    Edwards, A.L.4    Longino, J.T.5    Daly, J.W.6
  • 12
    • 3042656762 scopus 로고    scopus 로고
    • N. Toyooka, A. Fukutome, H. Nemoto, J. W. Daly, T. F. Spande, H. M. Garraffo and T. Kaneko, Org. Lett., 2002, 4, 1715-1717; N. Toyooka, A. Fukutome, H. Shinoda and H. Nemoto, Tetrahedron, 2004, 60, 6197-6216.
    • (2004) Tetrahedron , vol.60 , pp. 6197-6216
    • Toyooka, N.1    Fukutome, A.2    Shinoda, H.3    Nemoto, H.4
  • 19
    • 0025818883 scopus 로고
    • S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1991, 2, 183-186; J. F. Costello, S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1994, 5, 1999-2008.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 183-186
    • Davies, S.G.1    Ichihara, O.2
  • 22
    • 0000134173 scopus 로고
    • B. M. Trost, ed., Pergamon Press, Oxford
    • (b) K. Shiosaki, in Comprehensive Organic Synthesis, B. M. Trost, ed., Pergamon Press, Oxford, 1991, vol. 2, pp. 865-892.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 865-892
    • Shiosaki, K.1
  • 28
    • 0001813833 scopus 로고
    • S. G. Davies, O. Ichihara and I. A. S. Walters, J. Chem. Soc., Perkin Trans. 1, 1994, 1141-1147; S. G. Davies, O. Ichihara and I. A. S. Walters, Synlett, 1994, 117-118.
    • (1994) Synlett , pp. 117-118
    • Davies, S.G.1    Ichihara, O.2    Walters, I.A.S.3
  • 41
    • 15244347418 scopus 로고    scopus 로고
    • note
    • In a more closely related example, (±)-ethyl (5R*,8S*, 8aS*)-7-oxo-5-pentylindolizidine-8-carboxylate was readily converted into its 1,3-dithiane derivative in 87% yield upon treatment with Propane1,3-dithiol and boron trifluoride etherate in trifluoroacetic acid at ambient temperature: J. P. Michael and D. Gravestock, unpublished results.
  • 42
    • 10844226564 scopus 로고    scopus 로고
    • A further synthetic approach to indolizidine 223A and congeners was reported after this manuscript was submitted
    • A further synthetic approach to indolizidine 223A and congeners was reported after this manuscript was submitted: R. Kumareswaran, J. Gallucci and T. V. RajanBabu, J. Org. Chem., 2004, 69, 9151-9158.
    • (2004) J. Org. Chem. , vol.69 , pp. 9151-9158
    • Kumareswaran, R.1    Gallucci, J.2    Rajanbabu, T.V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.