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Analogues and surrogates of nectrisine with a similar pharmacological profile have also been prepared. See: (a) Tschamber, T.; Gessier, F.; Neuburger, M.; Gurcha, S. S.; Besra, G. S.; Streith, J. Eur. J. Org. Chem. 2003, 2792-2798.
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53049100530
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The stereochemical course of the reduction of 9 was assumed to be as depicted in Scheme 2 upon reliance on the results in the reduction of a ketone closely related to 9 (with an alkyl residue instead of the aryl group), where the configuration of the alcohol was secured by means of X-ray diffraction (unpublished results).
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The stereochemical course of the reduction of 9 was assumed to be as depicted in Scheme 2 upon reliance on the results in the reduction of a ketone closely related to 9 (with an alkyl residue instead of the aryl group), where the configuration of the alcohol was secured by means of X-ray diffraction (unpublished results).
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0033942849
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53049102983
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This idea was suggested by the fact that acidic treatment of alcohol 10 under similar conditions as 4 (TFA, 1 h, 0°C) also gave a 2:1 mixture of pyrrolidines 11, together with extensive decomposition
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This idea was suggested by the fact that acidic treatment of alcohol 10 under similar conditions as 4 (TFA, 1 h, 0°C) also gave a 2:1 mixture of pyrrolidines 11, together with extensive decomposition.
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53049109407
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Mixtures of 2 and 13 (5-epi-radicamine B) of variable composition were obtained, with the undesired 13 being always the major compound.
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Mixtures of 2 and 13 (5-epi-radicamine B) of variable composition were obtained, with the undesired 13 being always the major compound.
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34249110615
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For a synthesis of 13, see: Zhou, X.; Liu, W.-J.; Ye, J.-L.; Huang, P.-Q. Tetrahedron 2007, 63, 6346-6357.
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For a synthesis of 13, see: Zhou, X.; Liu, W.-J.; Ye, J.-L.; Huang, P.-Q. Tetrahedron 2007, 63, 6346-6357.
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For a similar situation, see for example
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For a similar situation, see for example: Yu, D.-S.; Xu, W.-X.; Liu, L.-X.; Huang, P.-Q. Synlett 2008, 1189-1192.
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Yu, D.-S.1
Xu, W.-X.2
Liu, L.-X.3
Huang, P.-Q.4
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Hulme, A. N.; Montgomery, C. H.; Henderson, D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1837-1841.
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Hulme, A.N.1
Montgomery, C.H.2
Henderson, D.K.3
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79
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53049106808
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The syntheses reported in ref 7g, 9 involve reaction sequences of 9-11 steps from D-xylose, L-xylose, or L-arabinose as the starting materials. Overall yields were in the range from 8 to 17%.
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The syntheses reported in ref 7g, 9 involve reaction sequences of 9-11 steps from D-xylose, L-xylose, or L-arabinose as the starting materials. Overall yields were in the range from 8 to 17%.
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