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Volumn 18, Issue 12, 2007, Pages 1410-1418

First asymmetric synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIPHENYL 3,7 BIS(1 PHENYLETHYL) 3,7 DIAZABICYCLO[3.3.1]NONANE; BISPIDINE DERIVATIVE; CARBENOID; CYCLOALKANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34447558354     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.06.010     Document Type: Article
Times cited : (9)

References (87)
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    • For the synthesis and application of bispidines with chiral side chains at the nitrogen atoms, see:
    • For the synthesis and application of bispidines with chiral side chains at the nitrogen atoms, see:. Huttenloch O., Spieler J., and Waldmann H. Chem. Eur. J. 7 (2001) 671-675
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  • 12
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    • 1-symmetric 2-phenyl-9-oxabispidines, see:
    • 1-symmetric 2-phenyl-9-oxabispidines, see:. Breuning M., and Steiner M. Synthesis (2007) 1702-1706
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    • For a recent application in natural product synthesis, see:
    • For a recent application in natural product synthesis, see:. Tambar U.K., Ebner D.C., and Stoltz B.M. J. Am. Chem. Soc. 128 (2006) 11752-11753
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    • Tambar, U.K.1    Ebner, D.C.2    Stoltz, B.M.3
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    • The alkaloid (+)-sparteine (+)-1 is also a natural product, albeit with a low abundance:
    • The alkaloid (+)-sparteine (+)-1 is also a natural product, albeit with a low abundance:. Orechoff A., Rabinowitch M., and Kolowanowa R. Ber. Dtsch. Chem. Ges. 66 (1933) 621-625
    • (1933) Ber. Dtsch. Chem. Ges. , vol.66 , pp. 621-625
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    • (+)-Sparteine (+)-1 can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine, see:
    • (+)-Sparteine (+)-1 can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine, see:. Ebner T., Eichelbaum M., Fischer P., and Meese C.O. Arch. Pharm. (Weinheim) 322 (1989) 399-403
    • (1989) Arch. Pharm. (Weinheim) , vol.322 , pp. 399-403
    • Ebner, T.1    Eichelbaum, M.2    Fischer, P.3    Meese, C.O.4
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    • Manske R.H.F., and Holmes H.L. (Eds), Academic Press, New York
    • Leonard N.J. In: Manske R.H.F., and Holmes H.L. (Eds). The Alkaloids, Chemistry and Physiology Vol. III (1953), Academic Press, New York 119-199
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    • Leonard, N.J.1
  • 61
    • 33846543653 scopus 로고    scopus 로고
    • For a review, see:
    • For a review, see:. Stead D., and O'Brien P. Tetrahedron 63 (2007) 1885-1897
    • (2007) Tetrahedron , vol.63 , pp. 1885-1897
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  • 63
    • 0000927272 scopus 로고
    • 2-symmetric bispidine α-isosparteine, which can be obtained by epimerisation of (-)-sparteine [(-)-1], see:
    • 2-symmetric bispidine α-isosparteine, which can be obtained by epimerisation of (-)-sparteine [(-)-1], see:. Galinovsky F., Knoth P., and Fischer W. Monatsh. Chem. 86 (1955) 1014-1023
    • (1955) Monatsh. Chem. , vol.86 , pp. 1014-1023
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    • For a related sequence within the total synthesis of (-)-sparteine [(-)-1], see Ref. 19.
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    • For the highly diastereoselective preparation of the enantiomer of 8, see:
    • For the highly diastereoselective preparation of the enantiomer of 8, see:. Davies S.G., and Walters I.A.S. J. Chem. Soc., Perkin Trans. 1 (1994) 1129-1140
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1129-1140
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    • Ref. 25a.
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    • note
    • 2OEt, which, however, possesses two leaving groups with a strongly different reactivity, was successfully added to an homopipecolic ester, see Ref. 19.
  • 81
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    • Many examples are known, in which 3-[N-benzyl-N-((S/R)-1-phenylethyl)amino]-3-phenylpropionates are selectively hydrogenated to give the corresponding N-deprotected 3-amino-3-phenylpropionates in high yields, see:
    • Many examples are known, in which 3-[N-benzyl-N-((S/R)-1-phenylethyl)amino]-3-phenylpropionates are selectively hydrogenated to give the corresponding N-deprotected 3-amino-3-phenylpropionates in high yields, see:. Davies S.G., Osamu I., and Walters I.A.S. J. Chem. Soc., Perkin Trans. 1 (1994) 1141-1147
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1141-1147
    • Davies, S.G.1    Osamu, I.2    Walters, I.A.S.3
  • 86
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    • Refs. 25a, 27b and 33a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.