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For recent reviews about natural occurrence, biological activity and therapeutic applications of natural hydroxylated pyrrolidines, see: N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1645 1680
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For a review on recent advances in the synthesis of naturally occurring polyhydroxylated alkaloids, see: H. Yoda Curr. Org. Chem. 6 2002 223 243
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P. Merino, T. Tejero, J. Revuelta, P. Romero, S. Cicchi, V. Mannucci, A. Brandi, and A. Goti Tetrahedron: Asymmetry 14 2003 367 379
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Tejero, T.2
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Cicchi, S.5
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Goti, A.8
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Merino, P.6
Tejero, T.7
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0142169426
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For a recent review about synthesis of 2-hydroxymethyl pyrrolidines, see: E.-S.H. El-Ashry, and A. El Nemr Carbohydr. Res. 338 2003 2265 2290 and references cited therein
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T. Sifferlen, A. Defoin, J. Streith, D. Le Nouën, C. Tarnus, I. Dosbaâ, and M.-J. Foglietti Tetrahedron 56 2000 971 978
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Le Nouën, D.4
Tarnus, C.5
Dosbaâ, I.6
Foglietti, M.-J.7
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W.O. Moss, R.H. Bradbury, N.J. Hales, and T. Gallagher J. Chem. Soc., Perkin Trans. 1 1992 1901 1906
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G.W.J. Fleet, J.C. Son, D.St.C. Green, I. Cenci di Bello, and B. Winchester Tetrahedron 44 1988 2649 2655
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Son, J.C.2
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Winchester, B.5
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G.N. Austin, P.D. Baird, G.W.J. Fleet, J.M. Peach, P.W. Smith, and D.J. Watkin Tetrahedron 43 1987 3095 3108
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Austin, G.N.1
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28
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0036180550
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For biological data on 2-hydroxymethyl-3,4-dihydroxypyrrolidines, see: K. Yasuda, H. Kizu, T. Yamashita, Y. Kameda, A. Kato, R.J. Nash, G.W.J. Fleet, R.J. Molyneux, and N. Asano J. Nat. Prod. 65 2002 198 202
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Kizu, H.2
Yamashita, T.3
Kameda, Y.4
Kato, A.5
Nash, R.J.6
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Molyneux, R.J.8
Asano, N.9
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F. Popowycz, S. Gerber-Lemaire, R. Demange, E. Rodriguez-Garcia, A.T.C. Asenjo, I. Robina, and P. Vogel Bioorg. Med. Chem. Lett. 11 2001 2489 2493
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Asenjo, A.T.C.5
Robina, I.6
Vogel, P.7
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37
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13244285756
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note
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2O) δ 36.6 (C-1′), 48.2 (C-5), 57.2 (C-2), 69.8 (C-4), 70.0 (C-3)
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38
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4544257545
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For a related example of inversion of configuration at C-2 of an N-hydroxypyrrolidine, see: P. Merino, J. Revuelta, T. Tejero, S. Cicchi, and A. Goti Eur. J. Org. Chem. 2004 776 782
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(2004)
Eur. J. Org. Chem.
, pp. 776-782
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Merino, P.1
Revuelta, J.2
Tejero, T.3
Cicchi, S.4
Goti, A.5
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40
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13244285835
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note
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Vinyl magnesium bromide addition to a related chiral cyclic nitrone followed by conversion of vinyl to hydroxymethyl through oxidative cleavage of CC double bond and reduction has been reported: Ref. 6f
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41
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0037074092
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2OMOM to acyclic nitrones has been reported: P. Merino, S. Franco, F.L. Merchan, J. Revuelta, and T. Tejero Tetrahedron Lett. 43 2002 459 462
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 459-462
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Merino, P.1
Franco, S.2
Merchan, F.L.3
Revuelta, J.4
Tejero, T.5
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42
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13244280523
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note
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13C NMR data of compounds 10 and 14 match those reported in the literature. The different assignment to protons at C-5 and C-1′, which are inverted, is based on bidimensional g-HMQC spectra, which unequivocally establish correlations of those protons with the connected carbon atoms
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