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1
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84977247933
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(-)-Sparteine (-)-1, also known as lupinidine, was first isolated in 1851:
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(-)-Sparteine (-)-1, also known as lupinidine, was first isolated in 1851:. Stenhouse J. Ann. Chem. Pharm. 78 (1851) 1-30
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(1851)
Ann. Chem. Pharm.
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Stenhouse, J.1
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3
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37049170337
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The structure of (-)-1 was elucidated in 1933
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The structure of (-)-1 was elucidated in 1933. Clemo G.R., and Raper R. J. Chem. Soc. (1933) 644-645
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(1933)
J. Chem. Soc.
, pp. 644-645
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Clemo, G.R.1
Raper, R.2
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5
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0344799549
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Hoppe D., Hintze F., Tebben P., Paetow M., Ahrens H., Schwerdtfeger J., Sommerfeld P., Haller J., Guarnieri W., Kolczewksi S., Hense T., and Hoppe I. Pure Appl. Chem. 66 (1994) 1479-1486
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Pure Appl. Chem.
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Hoppe, D.1
Hintze, F.2
Tebben, P.3
Paetow, M.4
Ahrens, H.5
Schwerdtfeger, J.6
Sommerfeld, P.7
Haller, J.8
Guarnieri, W.9
Kolczewksi, S.10
Hense, T.11
Hoppe, I.12
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9
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18844414256
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Rappoport Z., and Marek I. (Eds), Wiley, Chichester
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Gawley R.E., and Coldham I. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds (2004), Wiley, Chichester 997-1053
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The Chemistry of Organolithium Compounds
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Gawley, R.E.1
Coldham, I.2
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10
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18844423506
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Rappoport Z., and Marek I. (Eds), Wiley, Chichester
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Hoppe D., and Christoph G. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds (2004), Wiley, Chichester 1055-1164
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(2004)
The Chemistry of Organolithium Compounds
, pp. 1055-1164
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Hoppe, D.1
Christoph, G.2
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11
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33745832929
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Lemaire M., and Mangeney P. (Eds), Springer, Berlin
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Chuzel O., and Riant O. In: Lemaire M., and Mangeney P. (Eds). Topics in Organometallic Chemistry Vol. 15 (2005), Springer, Berlin 59-92
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(2005)
Topics in Organometallic Chemistry
, vol.15
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Chuzel, O.1
Riant, O.2
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13
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50649097976
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Sorger, K.; Petersen, H.; Stohrer, J. U.S. Patent 6,924,386, 2005.
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Sorger, K.; Petersen, H.; Stohrer, J. U.S. Patent 6,924,386, 2005.
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14
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0000941482
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For earlier (-)-sparteine-mediated Reformatsky reactions see:
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For earlier (-)-sparteine-mediated Reformatsky reactions see:. Guetté M., Capillon J., and Guetté J.-P. Tetrahedron 29 (1973) 3659-3667
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(1973)
Tetrahedron
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Guetté, M.1
Capillon, J.2
Guetté, J.-P.3
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17
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33749535618
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Maheswaran H., Prasanth K.L., Krishna G.G., Ravikumar K., Sridhar B., and Kantam M.L. Chem. Commun. (2006) 4066-4068
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(2006)
Chem. Commun.
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Maheswaran, H.1
Prasanth, K.L.2
Krishna, G.G.3
Ravikumar, K.4
Sridhar, B.5
Kantam, M.L.6
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24
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52049096917
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10.1002/anie.200801865 early view
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Ebner D.C., Trend R.M., Genet C., McGrath M.J., O'Brien P., and Stoltz B.M. Angew. Chem., Int. Ed. (2008) 10.1002/anie.200801865 early view
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(2008)
Angew. Chem., Int. Ed.
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Ebner, D.C.1
Trend, R.M.2
Genet, C.3
McGrath, M.J.4
O'Brien, P.5
Stoltz, B.M.6
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25
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0042352255
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Zhang Y., Yeung S.-M., Wu H., Heller D.P., Wu C., and Wulff W.D. Org. Lett. 5 (2003) 1813-1816
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(2003)
Org. Lett.
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Zhang, Y.1
Yeung, S.-M.2
Wu, H.3
Heller, D.P.4
Wu, C.5
Wulff, W.D.6
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28
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0344084118
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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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Org. Biomol. Chem.
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Hermet, J.-P.R.1
Porter, D.W.2
Dearden, M.J.3
Harrison, J.R.4
Koplin, T.5
O'Brien, P.6
Parmene, J.7
Tyurin, V.8
Whitwood, A.C.9
Gilday, J.10
Smith, N.M.11
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29
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0345425567
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(+)-Sparteine (+)-1, also known as pachycarpine, was first isolated in 1933 from Sophora pachycarpa C. A. Mey:
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(+)-Sparteine (+)-1, also known as pachycarpine, was first isolated in 1933 from Sophora pachycarpa C. A. Mey:. Orechoff A., Rabinowitch M., and Konowalowa R. Ber. Dtsch. Chem. Ges. 66 (1933) 621-625
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(1933)
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Orechoff, A.1
Rabinowitch, M.2
Konowalowa, R.3
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30
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0024697050
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It can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine (rac-10-oxosparteine), see:
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It can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine (rac-10-oxosparteine), see:. Ebner T., Eichelbaum M., Fischer P., and Meese C.O. Arch. Pharm. (Weinheim) 322 (1989) 399-403
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(1989)
Arch. Pharm. (Weinheim)
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Ebner, T.1
Eichelbaum, M.2
Fischer, P.3
Meese, C.O.4
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33
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4043120293
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For the synthesis of N-alkyl derivatives of 2 from 3, see:
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For the synthesis of N-alkyl derivatives of 2 from 3, see:. Dearden M.J., McGrath M.J., and O'Brien P. J. Org. Chem. 69 (2004) 5789-5792
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(2004)
J. Org. Chem.
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Dearden, M.J.1
McGrath, M.J.2
O'Brien, P.3
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35
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31444441304
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Wilkinson J.A., Rossington S.B., Ducki S., Leonard J., and Hussain N. Tetrahedron 62 (2006) 1833-1844
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(2006)
Tetrahedron
, vol.62
, pp. 1833-1844
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Wilkinson, J.A.1
Rossington, S.B.2
Ducki, S.3
Leonard, J.4
Hussain, N.5
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38
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0037201152
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Danieli B., Lesma G., Passarella D., Piacenti P., Sacchetti A., Silvani A., and Virdis A. Tetrahedron Lett. 43 (2002) 7155-7158
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(2002)
Tetrahedron Lett.
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, pp. 7155-7158
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Danieli, B.1
Lesma, G.2
Passarella, D.3
Piacenti, P.4
Sacchetti, A.5
Silvani, A.6
Virdis, A.7
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Danieli B., Lesma G., Passarella D., Sacchetti A., and Silvani A. Tetrahedron Lett. 46 (2005) 7121-7123
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Tetrahedron Lett.
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Danieli, B.1
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Sacchetti, A.4
Silvani, A.5
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40
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35748969108
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Hermet J.-P.R., Viterisi A., Wright J.M., McGrath M.J., O'Brien P., Whitwood A.C., and Gilday J. Org. Biomol. Chem. 5 (2007) 3614-3622
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Org. Biomol. Chem.
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Hermet, J.-P.R.1
Viterisi, A.2
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McGrath, M.J.4
O'Brien, P.5
Whitwood, A.C.6
Gilday, J.7
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41
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0001147659
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For the stereoselective synthesis of other bispidines possessing a chirally modified core, see:
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For the stereoselective synthesis of other bispidines possessing a chirally modified core, see:. Smith B.T., Wendt J.A., and Aubé J. Org. Lett. 4 (2002) 2577-2579
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(2002)
Org. Lett.
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Smith, B.T.1
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Aubé, J.3
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Hermet J.-P.R., McGrath M.J., O'Brien P., Porter D.W., and Gilday J. Chem. Commun. (2004) 1830-1831
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Chem. Commun.
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Hermet, J.-P.R.1
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Gilday, J.5
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46
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50649086665
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note
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There is a single abstract of a lecture by Gill et al. held at the 232nd ACS National Meeting, in which an enantioselective route to 6 and some other bicyclic 9-oxabispidines of type 4 is sketched. However, no yields or characterization data are given, see: Gill, D. M.; Holness, H.; Keegan, P. S. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, 2006.
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note
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It should be noted that due to the additional oxygen atom in 4, a competing N,O-complexation of metals might occur. Preliminary quantum chemical calculations, however, showed such a complexation to be strongly disfavored as compared to the N,N-complexation of metals.
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Ref. 16b.
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Ref. 16b.
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59
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0024231266
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for the HCl-salt of 9b, see:
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for the HCl-salt of 9b, see:. Thurkauf A., Zenk P.C., Balster R.L., May E.L., George C., Carroll F.I., Mascarella S.W., Rice K.C., Jacobson A.E., and Mattson M.V. J. Med. Chem. 31 (1988) 2257-2263
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Thurkauf, A.1
Zenk, P.C.2
Balster, R.L.3
May, E.L.4
George, C.5
Carroll, F.I.6
Mascarella, S.W.7
Rice, K.C.8
Jacobson, A.E.9
Mattson, M.V.10
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