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For a pertinent review on spectinomycin, see: W. Rosenbrook, Jr., J. Antibiot. 1979, 32, S211-S227.
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Rosenbrook Jr., W.1
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Pozgay, V.1
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a) G. Ekborg, P. J. Garegg, S. Josephson, Carbohydr. Res. 1978, 65, 301-306;
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33645198473
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See ref. [9] (footnote 19 therein)
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c) See ref. [9] (footnote 19 therein).
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27
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0026576695
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F. W. Lichtenthaler, U. Kläres, M. Lergenmüller, S. Schwidetzky, Synthesis 1992, 179-184.
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33645200720
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note
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The alternative possibility, cyclo-hemiketalization of 13 by OH→C=O attack from the upper (equatorial) face would lead to the sterically and thermodynamically unfavorable trans-transoid-trans-fused product in which the central dioxane ring is forced into a boat (or twist-boat) conformation.
-
-
-
-
29
-
-
0022479554
-
-
Racemic 16, in noncrystalline form, has previously been prepared through elaboration of the pyranoid portion through an aldehyde/diene cycloaddition approach: S. Danishefsky, J. Aubé, M. Bednarski, J. Am. Chem. Soc. 1986, 108, 4145-4149.
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Danishefsky, S.1
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30
-
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0016647353
-
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Gomphogenin (17) was prepared from digitoxin by hydrolytic removal of the sugars and conversion of its aglycon, digitoxigenin, through a known seven-step procedure: Y. Kamano, G. R. Pettit, M. Tozawa, J. Chem. Soc. Perkin Trans. 1 1975, 1972-1976;
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Kamano, Y.1
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37049102090
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J. F. Templeton, H. T. A. Cheung, C. R. Sham, T. R. Watson, J. Chem. Soc. Perkin Trans. 1 1983, 251-256.
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32
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0016689897
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The catalyst was adapted from the Ru/C-mediated hydrogenation of spectinomycin (7), which provided an epimeric mixture mainly consisting of the (4R)-dihydro analogue 8: W. Rosenbrook, Jr., R. E. Carney, J. Antibiot. 1975, 28, 953-959.
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Rosenbrook Jr., W.1
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35
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33645203454
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note
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2, which accounts for the comparatively large difference in melting behavior.
-
-
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36
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0017758481
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T. Suami, S. Nishiyama, H. Ishikawa, H. Okada, T. Kinoshita, Bull. Chem. Soc. Jpn. 1977, 50, 2754-2757.
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45949117596
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a) C. A. A. van Boeckel, T. Beetz, A. C. Kock-van Dalen, H. van Bekkum, Recl. Trav. Chim. Pays-Bas 1987, 106, 596-598;
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Van Boeckel, C.A.A.1
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39
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33645197684
-
-
note
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The less reactive ulosyl bromide (11) gave complex mixtures under these conditions which contained substantial amounts of 21.
-
-
-
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40
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0027499404
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0019119717
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