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a) A similar case is observed in carbohydrates: the formation of α-iodo glycosides is far more difficult, due to their instability, than the generation of the α-bromo or α-chloro analogues. For recent comments on the subject, see: N. Miquel, S. Vignando, G. Russo, L. Lay, Synlett 2004, 341-343;
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46
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15144357943
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Acid 13: M. Rowley, I. Collins, H. B. Broughton, W. B. Davey, R. Baker, F. Emms, R. Marwood, S. Patel, S. Patel, C. I. Ragan, S. B. Freedman, R. Ball, P. D. Leeson, J. Med. Chem. 1997, 40, 2374-2385.
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50
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0035804301
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14944341808
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Compound 17 is also available from Aldrich
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Compound 17 is also available from Aldrich.
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53
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0037030612
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Compound 18: B. Froelund, A. T. Joergensen, L. Tagmose, T. B. Stensboel, H. T. Vestergaard, C. Engblom, U. Kristiansen, C. Sanchez, P. Krogsgaard-Larsen, T. Liljefors, J. Med. Chem. 2002, 45, 2454-2468.
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15444342053
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G. I. Stevenson, I. Huscroft, A. M. McLeod, C. J. Swain, M. A. Cascieri, G. G. Chicchi, M. I. Graham, T. Harrison, F. J. Kelleher, M. Kurtz, T. Ladduwahetty, K. J. Merchant, J. M. Metzger, D. E. MacIntyre, S. Sadowski, B. Sohal, A. P. Owens, J. Med. Chem. 1998, 41, 4623-4635.
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55
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18244423945
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For an alternative synthesis of acid 25, see: T. P. Burkholder. E. M. Kudlacz, G. D. Maynard, X.-G. Liu, T.-B. Le, M. E. Webster, S. W. Horgan, D. L. Wenstrup, D. W. Freund, F. Boyer, L. Bratton, R. S. Gross, R. W. Knippenberg, D. E. Logan, B. K. Jones, T. M. Chen, Bioorg. Mol. Med. Chem. 1997, 7, 2531-2536.
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66
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10744227527
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14944362463
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note
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C = 41.6 ppm).
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91
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14944386671
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note
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3 solution, which was then extracted with EtOAc. The organic layer was dried, filtered and the solvents evaporated under vacuum to afford the free tetrahydroisoquinoline.
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