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Breuning, M.1
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0345425567
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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
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(+)-Sparteine (+)-1 can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine, see:
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(+)-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
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For the preparation of (+)-2, see also:
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For the preparation of (+)-2, see also:. Hermet J.-P.R., Porter D.W., Dearden M.J., Harrison J.R., Koplin T., O'Brien P., Parmene J., Tyurin V., Whitwood A.C., Gilday J., and Smith N.M. Org. Biomol. Chem. 1 (2003) 3977-3988
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63
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2-symmetric bispidine α-isosparteine, which can be obtained by epimerisation of (-)-sparteine [(-)-1], see:
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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
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34447576371
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For a related sequence within the total synthesis of (-)-sparteine [(-)-1], see Ref. 19.
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66
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37049071174
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For the highly diastereoselective preparation of the enantiomer of 8, see:
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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
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68
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For a less diastereoselective preparation of 8 at 0 °C, see:
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Ref. 25a.
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note
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2OEt, which, however, possesses two leaving groups with a strongly different reactivity, was successfully added to an homopipecolic ester, see Ref. 19.
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78
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Bull, S.D.1
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37049081663
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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
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