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Aminocyclitol antibiotics
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2: K.A. Andrianov, N.V. Delazari, Dokl. Akad. Nauk. SSSR 1958, 122, 393 (Chem. Abstr. 1959, 53, 2133).
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33
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0041396332
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note
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It is noteworthy that the second dihydroxylation occurred exclusively syn relative to the silicon group.
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34
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85128572654
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note
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1H-NMR of Mosher's esters prepared from alcohol 8.
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35
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0042899439
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note
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When epoxidation was carried out using (+)-DET ((+)-diethyl tartrate), the conversion was complete after only 4 d, illustrating the important difference in reactivity between the 'matched' and the 'mis-matched' pair.
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37
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33845557645
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b) D.J. Morgans, Jr., K.B. Sharpless, S.G. Traynor, J. Am. Chem. Soc. 1981, 103, 462.
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Morgans D.J., Jr.1
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38
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0028330925
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For previous asymmetric syntheses of conduritol-E(11), see: a) S. Takano, T. Yoshimitsu, K. Ogasawara, J. Org. Chem. 1994, 59, 54;
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37049088912
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b) T. Hudlicky, H. Luna, H.F. Olivo, C. Andersen, T. Nugent, J.D. Price, J. Chem. Soc., Perkin Trans. 1 1991, 2907.
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41
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70350650110
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For a similar approach, see: X. Deruyttere, L. Dumortier, J. Van der Eycken, M. Vandewalle, Synlett 1992, 51.
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Deruyttere, X.1
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0000640476
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Two enantioselective syntheses of (+)-palitantin ((+)-14) have been reported to date and were found to be less efficient in term of yields and number of steps [22]: S. Hanessian, Y. Sakito, D. Dhanoa, L. Baptistella, Tetrahedron 1989, 45, 6623.
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45
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0000269981
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The ring epoxide opening followed a transdiaxial mode, thus obeying the Fürst-Plattner rule: A. Fürst, P.A. Plattner, Helv. Chim. Acta 1949, 32, 275.
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Fürst, A.1
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46
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0001517733
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For previous asymmetric syntheses of 2-deoxy-allo-inositol (17), see: a) G.E. McCasland, S. Furuta, L.F. Johnson, J.N. Shoolery, J. Am. Chem. Soc. 1961, 83, 2335;
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0001056910
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M. Hirama, M. Iwashita, Y. Yamazaki, S. Ito, Tetrahedron Lett. 1984, 25, 4963.
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33748233248
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a) G. Li. H.-T. Chang, K.B. Sharpless, Angew. Chem., Int. Ed. Engl. 1996, 35, 451;
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b) J. Rudolph, P.C. Sennhenn, C.P. Vlaar, K.B. Sharpless, ibid. 1996, 35, 2810;
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Rudolph, J.1
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0030484915
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c) G. Li, H.H. Angert, K.B. Sharpless, ibid. 1996, 35, 2813.
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62
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85128584020
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note
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4) were carried out, unfortunately leading to complex mixtures.
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64
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0011388902
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For a review on the [2,3]-Wittig rearrangement, see: T. Mikami, T. Nakai, Synthesis 1992, 234.
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66
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0041897295
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note
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It is worthnoting that Peterson elimination (at C(2)/C(3), 40) did not occur under these conditions.
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69
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0009110079
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70
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85128548861
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note
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2SiCl (3) at low temperature.
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72
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0042899434
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85128543548
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note
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2)).
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