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Volumn , Issue 16, 2005, Pages 3461-3468

Synthesis of alkaloid analogues from α-amino acids by one-pot radical decarboxylation/alkylation

Author keywords

Alkaloids; Amino acids; Nitrogen heterocycles; Radical reactions; Spiro compounds

Indexed keywords


EID: 23944472481     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500124     Document Type: Article
Times cited : (25)

References (123)
  • 9
    • 0035232404 scopus 로고    scopus 로고
    • Simple Indolizidine and Quinolizidine Alkaloids
    • (Ed.; G. Cordell), Academic Press, New York
    • c) J. P. Michael, "Simple Indolizidine and Quinolizidine Alkaloids", in The Alkaloids, Chemistry and Pharmacology (Ed.; G. Cordell), Academic Press, New York, 2001, vol. 55, pp. 91-258;
    • (2001) The Alkaloids, Chemistry and Pharmacology , vol.55 , pp. 91-258
    • Michael, J.P.1
  • 12
    • 0034721683 scopus 로고    scopus 로고
    • and references cited therein
    • f) A. El Nemr, Tetrahedron 2000, 56, 8579-8629, and references cited therein.
    • (2000) Tetrahedron , vol.56 , pp. 8579-8629
    • El Nemr, A.1
  • 15
    • 0001733739 scopus 로고
    • and references cited therein
    • c) C. Vogel, S. J. Danishefsky, J. Org. Chem. 1986, 51, 3915-3916, and references cited therein.
    • (1986) J. Org. Chem. , vol.51 , pp. 3915-3916
    • Vogel, C.1    Danishefsky, S.J.2
  • 22
    • 2942574530 scopus 로고    scopus 로고
    • For reviews concerning acyliminium ions, see: a) J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311-2352;
    • (2004) Chem. Rev. , vol.104 , pp. 2311-2352
    • Royer, J.1    Bonin, M.2    Micouin, L.3
  • 29
    • 0001673091 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford
    • h) H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Chemistry (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, vol. 2, pp. 1047-1082;
    • (1991) Comprehensive Organic Chemistry , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 30
    • 0000997425 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford
    • i) L. E. Overman, D. J. Ricca, in Comprehensive Organic Chemistry (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, vol. 2, pp. 1007-1046;
    • (1991) Comprehensive Organic Chemistry , vol.2 , pp. 1007-1046
    • Overman, L.E.1    Ricca, D.J.2
  • 31
    • 77957077000 scopus 로고
    • (Ed.: A. Brossi), Academic Press, New York
    • j) H. De Koning, W. N. Speckamp, in The Alkaloids (Ed.: A. Brossi), Academic Press, New York, 1988; vol. 32, pp. 271-339;
    • (1988) The Alkaloids , vol.32 , pp. 271-339
    • De Koning, H.1    Speckamp, W.N.2
  • 43
    • 0004230722 scopus 로고
    • (Ed.: R. H. F. Manske), Academic Press, New York, chapter 3
    • a) For reviews which detail the biological activities (including antitumoural activity) of these alkaloids, see: I. R. C. Bick, W. Sinchai, in The Alkaloids (Ed.: R. H. F. Manske), Academic Press, New York, 1981, vol XIX, chapter 3;
    • (1981) The Alkaloids , vol.19
    • Bick, I.R.C.1    Sinchai, W.2
  • 44
    • 0002269682 scopus 로고
    • (Ed.: A. Brossi), Academic Press, Orlando
    • b) M. Suffness, G. A. Cordell, in The Alkaloids (Ed.: A. Brossi), Academic Press, Orlando, 1985, vol. 25, pp. 3-355.
    • (1985) The Alkaloids , vol.25 , pp. 3-355
    • Suffness, M.1    Cordell, G.A.2
  • 61
    • 23944484268 scopus 로고    scopus 로고
    • note
    • 2,3 = 8.0, 9.1 Hz. It must be taken into account that free rotation around the C2-C2′ bond is possible, and hence the experimental constants may not completely match those calculated for the minimum-energy conformations.
  • 62
    • 20444483055 scopus 로고
    • Theoretical coupling constants were calculated over the minimised structures (MMFF force field) for all possible isomers, by using the Karplus-Altona equation implemented in the Macromodel 7.0 program. See: C. A. G. Haasnoot, F. A. A. M. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783-2792.
    • (1980) Tetrahedron , vol.36 , pp. 2783-2792
    • Haasnoot, C.A.G.1    De Leeuw, F.A.A.M.2    Altona, C.3
  • 63
    • 23944456149 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum of the mixture resembles that of compound 19, and shows olefinic (C) signals corresponding either to another diastereomer or to double-bond position isomers. The estimated 81% yield was calculated from the weight of the mixture isolated after column chromatography.
  • 64
    • 23944499360 scopus 로고    scopus 로고
    • note
    • 10b,1 = 5.1, 11.6 Hz for the (10aR*,10bR*) diastereomer.
  • 68
    • 0035954860 scopus 로고    scopus 로고
    • and references cited therein
    • d) D. J. Wardrop, W. Zhang, Org. Lett. 2001, 3, 2353-2356, and references cited therein.
    • (2001) Org. Lett. , vol.3 , pp. 2353-2356
    • Wardrop, D.J.1    Zhang, W.2
  • 79
    • 0035515394 scopus 로고    scopus 로고
    • and references cited therein
    • For other interesting examples, see: a) T. J. Greshock, R. L. Funk, Org. Lett. 2001, 3, 3511-3514, and references cited therein;
    • (2001) Org. Lett. , vol.3 , pp. 3511-3514
    • Greshock, T.J.1    Funk, R.L.2
  • 85
    • 0010338473 scopus 로고
    • Acid 21: S. Elmore, Biochem. J. 1965, 94, 563-564.
    • (1965) Biochem. J. , vol.94 , pp. 563-564
    • Elmore, S.1
  • 86
    • 0001273637 scopus 로고    scopus 로고
    • and references cited therein
    • For a good summary on the generation of tertiary acyliminium ions and related problems, see: a) L. Ollero, G. Mentink, F. P. T. J. Rutjes, W. N. Speckamp, H. Hiemstra, Org. Lett. 1999, 1, 1331-1334, and references cited therein.
    • (1999) Org. Lett. , vol.1 , pp. 1331-1334
    • Ollero, L.1    Mentink, G.2    Rutjes, F.P.T.J.3    Speckamp, W.N.4    Hiemstra, H.5
  • 90


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.