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(f) Caines, M. E. C.; Hancock, S. M.; Tarling, C. A.; Wrodnigg, T. M.; Stick, R. V.; Stütz, A. E.; Vasella, A.; Withers, S. G.; Strynadka, N. C. J. Angew. Chem. Int. Ed. 2007, 46, 4474.
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(b) Compain, P.; Martin, O. R. Iminosugars: From Synthesis to Therapeutic Applications; Wiley: Chichester, 2007, in press.
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(e) Toyao, A.; Tamura, O.; Tagaki, H.; Ishibashi, H. Synlett 2003, 35.
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Toyao, A.1
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35648970633
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See also ref. 5 and 6
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(g) See also ref. 5 and 6.
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16
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0344944860
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Goti, A.; Cicchi, S.; Mannucci, V.; Cardona, F.; Guarna, F.; Merino, P.; Tejero, T. Org. Lett. 2003, 5, 4235.
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Goti, A.1
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Merino, P.6
Tejero, T.7
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33747748514
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Gurjar, M. K.; Borhade, R. G.; Puranik, V. G.; Ramana, C. V. Tetrahedron Lett. 2006, 47, 6979.
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Gurjar, M.K.1
Borhade, R.G.2
Puranik, V.G.3
Ramana, C.V.4
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19
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35648997522
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In their original papers, appeared during the preparation of this manuscript, Gurjar (ref. 5) and Yu (ref. 6) reported the synthesis of the enantiomers of the natural products since they started from ent-5, synthesizing ent-1 and ent-2. Indeed, Yu et al. (ref. 6) revised the configuration of both natural radicamines A and B as those given in Figure 1.
-
In their original papers, appeared during the preparation of this manuscript, Gurjar (ref. 5) and Yu (ref. 6) reported the synthesis of the enantiomers of the natural products since they started from ent-5, synthesizing ent-1 and ent-2. Indeed, Yu et al. (ref. 6) revised the configuration of both natural radicamines A and B as those given in Figure 1.
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20
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0037430434
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(a) Cardona, F.; Faggi, E.; Liguori, F.; Cacciarini, M.; Goti, A. Tetrahedron Lett. 2003, 44, 2315.
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Tetrahedron Lett
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Cardona, F.1
Faggi, E.2
Liguori, F.3
Cacciarini, M.4
Goti, A.5
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21
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0141989685
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(b) Carmona, A. T.; Whigtman, R. H.; Robina, I.; Vogel, P. Helv. Chim. Acta 2003, 86, 3066.
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Helv. Chim. Acta
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Carmona, A.T.1
Whigtman, R.H.2
Robina, I.3
Vogel, P.4
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22
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13844318446
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(c) Desvergnes, S.; Py, S.; Vallée, Y. J. Org. Chem. 2005, 70, 1459.
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J. Org. Chem
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Desvergnes, S.1
Py, S.2
Vallée, Y.3
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23
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33644536076
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(d) Cicchi, S.; Marradi, M.; Vogel, P.; Goti, A. J. Org. Chem. 2006, 71, 1614.
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J. Org. Chem
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Cicchi, S.1
Marradi, M.2
Vogel, P.3
Goti, A.4
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24
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33947518523
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(e) Revuelta, J.; Cicchi, S.; Goti, A.; Brandi, A. Synthesis 2007, 485.
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(2007)
Synthesis
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Revuelta, J.1
Cicchi, S.2
Goti, A.3
Brandi, A.4
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25
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35649024303
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Data for 8: [α]D20 +57 (c 1.11, H2O, 1H NMR (400 MHz, D2O, δ, 3.63 (ddd, J, 8.2, 5.5, 4.1 Hz, 1 H, H5, 3.83 (dd, J, 13.3, 6.3 Hz, 1 H, CH2OH, 3.88 (dd, J, 13.3, 4.5 Hz, 1 H, CH2OH, 4.11 (t, J, 7.5 Hz, 1 H, H4, 4.39 (d, J, 9.9 Hz, 1 H, H2, 4.43 (dd, J, 10.0, 6.9 Hz, 1 H, H3, 7.37-7.47 (m, 5 H, Ar, 13C NMR (100 MHz, D2O, δ, 58.1 (CH2OH, 61.9 (C2, 63.2 (C5, 73.7 (C3, 77.5 (C4, 128.3 (Ar, 128.5 (Ar, 130.3 (Ar, 131.3 Ar, Anal. Calcd for C11H 16NO3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.92; H, 6.74; N, 5.68
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3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.92; H, 6.74; N, 5.68.
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26
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13244299173
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Marradi, M.; Cicchi, S.; Delso, I.; Rosi, L.; Tejero, T.; Merino, P.; Goti, A. Tetrahedron Lett. 2005, 46, 1287.
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(2005)
Tetrahedron Lett
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, pp. 1287
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Marradi, M.1
Cicchi, S.2
Delso, I.3
Rosi, L.4
Tejero, T.5
Merino, P.6
Goti, A.7
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27
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0030969628
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(a) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem. 1997, 62, 3119.
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(1997)
J. Org. Chem
, vol.62
, pp. 3119
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Goti, A.1
Cicchi, S.2
Fedi, V.3
Nannelli, L.4
Brandi, A.5
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28
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0029162529
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(b) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743.
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(1995)
J. Org. Chem
, vol.60
, pp. 4743
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Cicchi, S.1
Goti, A.2
Brandi, A.3
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29
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35648990589
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f = -79.21 kcal/mol).
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f = -79.21 kcal/mol).
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30
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0035840368
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Cicchi, S.; Marradi, M.; Goti, A.; Brandi, A. Tetrahedron Lett. 2001, 42, 6503.
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(2001)
Tetrahedron Lett
, vol.42
, pp. 6503
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Cicchi, S.1
Marradi, M.2
Goti, A.3
Brandi, A.4
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31
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35648946901
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Data for 15: [α]D20 +45 (c 0.41, H2O, 1H NMR (400 MHz, D2O, δ, 3.86-3.96 (m, 3 H, H5, CH2OH, 4.35 (t, J, 3.3 Hz, 1 H, H4, 4.41 (d, J, 5.9 Hz, 1 H, H2, 4.49 (dd, J, 5.9, 3.1 Hz, 1 H, H3, 7.40-7.50 (m, 5 H, Ar, 13C NMR (100 MHz, D2O, δ, 56.9 (CH2OH, 62.9 (C2, 67.6 (C5, 74.5 (C3, 79.8 (C 4, 128.4 (Ar, 129.4 (Ar, 130.0 (Ar, 132.1 (Ar, Anal. Calcd for C11H16NO3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.70; H, 6.62; N, 5.79. Data for 16: [α]D 20 +78 (c 0.54, H2O, 1H NMR (400 MHz, D2O, δ, 3.64 (ddd, J, 8.4, 4.8, 3.5 Hz, 1 H, H 5, 3.85 dd, J, 12.2, 8.6 Hz, 1 H, CH2OH
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3Cl: C, 53.77; H, 6.56; N, 5.70. Found: C, 53.85; H, 6.40; N, 5.45.
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32
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0037375664
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Yu, Y.; Singh, S. K.; Liu, A.; Li, T.-K.; Liu, L. F.; LaVoice, E. J. Bioorg. Med. Chem. 2003, 11, 1475.
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(2003)
Bioorg. Med. Chem
, vol.11
, pp. 1475
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Yu, Y.1
Singh, S.K.2
Liu, A.3
Li, T.-K.4
Liu, L.F.5
LaVoice, E.J.6
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33
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4544257545
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Merino, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
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(2004)
Eur. J. Org. Chem
, pp. 776
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Merino, P.1
Revuelta, J.2
Tejero, T.3
Cicchi, S.4
Goti, A.5
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34
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35648969641
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Data for 2·HCl: [α]D20 +81 (c 0.25, H2O, 1H NMR (400 MHz, D2O, δ, 3.57 (ddd, J, 4.0, 6.2, 8.5 Hz, 1 H, H5, 3.81 (dd, J, 6.2, 12.6 Hz, 1 H, CH2OH, 3.86 (dd, J, 4.0, 12.6 Hz, 1 H, CH2OH, 4.08 (t, J, 7.7 Hz, 1 H, H4, 4.31 (d, J, 10.2 Hz, 1 H, H2, 4.37 (dd, J, 7.5, 10.2 Hz, 1 H, H3, 6.87 (d, J, 8.7 Hz, 2 H, ArH, 7.32 (d, J, 8.7 Hz, 2 H, ArH, 13C NMR (100 MHz, D 2O, d, 58.2 (CH2OH, 61.6 (C2, 62.8 (C 4, 73.6 (C3, 77.1 (C5, 116.2 (Ar, 122.9 (Ar, 130.2 (Ar, 157.1 (Ar, Anal. Calcd for C11H 16NO4Cl: C, 50.48; H, 6.48; N, 5.63. Found: C, 58.29; H, 6.73; N, 5.80. Data for 2: [α]D20 +74 c 0.29, H
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4: C, 58.66; H, 6.71; N, 6.22. Found: C, 58.50; H, 6.90; N, 6.31.
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