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(a) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. P.; Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097.
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11
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0442263682
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For instance, tubulin affinity is completely lost with the C-15 epimer, the C-6 epimer, and the C-8 epimer (ref 3a)
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For instance, tubulin affinity is completely lost with the C-15 epimer, the C-6 epimer, and the C-8 epimer (ref 3a).
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12
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0031906651
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Nicolaou, K. C.; Sarabia, F.; Ninkovic, S.; Finlay, M. R. V.; Boddy, C. N. C. Angew. Chem., Int. Ed. 1998, 37, 81.
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13
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0030889136
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(a) Meng, D.; Su, D.-S.; Balog, A.; Bertinano, P.; Sorensen, S. J., Danishefsky, S. J.; Zheng, T.-C.; He, L.; Horwitz, S. B. J. Am. Chem. Soc. 1997, 119, 2733.
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14
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0442265231
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PCT Int. Appl. WO9901124, 1999
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(b) Danishefsky, S. J.; Balog, A.; Bertinato, P.; Su, D.-S.; Chou, T.-C.; Meng, D. F.; Kamenecka, T.; Sorensen, E. J. PCT Int. Appl. WO9901124, 1999.
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Sorensen, E.J.8
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15
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0033551046
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Ojima, I.; Chakravarty, S.; Inoue, T.; Lin, S.; He, L.; Horwitz, S. B.; Kuduk, S. D.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4256.
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Danishefsky, S.8
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16
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0034692354
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Borzilleri, R. M.; Zheng, X.; Schmidt, R. J.; Johnson, J. A.; Kim, S.-H.; DiMarco, J. D.; Fairchild, C. R.; Gougoutas, J. Z.; Lee, F. Y. F.; Long, B. H.; Vite, G. D. J. Am. Chem. Soc. 2000, 122, 8890.
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DiMarco, J.D.6
Fairchild, C.R.7
Gougoutas, J.Z.8
Lee, F.Y.F.9
Long, B.H.10
Vite, G.D.11
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17
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0442263678
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The synthesis of 7 and 8 was first disclosed by Höfle and co-workers in patent literature (DE 19639456.2)
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The synthesis of 7 and 8 was first disclosed by Höfle and co-workers in patent literature (DE 19639456.2).
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18
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0442266807
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note
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The NOE pattern between epothilone A and B analogues with the same relative stereochemistry was remarkably similar. NOE effects between H-3 and H-6, H-3 and H-8, as well as H-3 and the adjacent methyl with a lower chemical shift could be observed for all (3S)-diastereoisomers.
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19
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0442268285
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note
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w = 0.065 for 1256 observed intensities (I > 3σ(I)), mp = 158-161 °C. Only one position is shown for some rotamerically disordered ethyls of the triethylsilyl group of 11. Crystallographic data (excluding structure factors) for the above compounds have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-190177, -190176. and -190178, respectively. Copies of the data can be obtained free of charge upon application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: (+44)1223-336-033. E-mail: deposit@ ccdc.cam.ac.uk).
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20
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0034678986
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Altmann, K.H.1
Wartmann, M.2
O'Reilly, T.3
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21
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0442265223
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95 refers to 5% degradation of compound in pH 1 buffer as determined by HPLC analysis
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95 refers to 5% degradation of compound in pH 1 buffer as determined by HPLC analysis.
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22
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0032213635
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Sefkow, M.; Kiffe, M.; Höfle, G. Bioorg. Med. Chem. Lett. 1998, 8, 3031.
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Sefkow, M.1
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23
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0442268286
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Regueiro-Ren, A.; Borzilleri, R. M.; Zheng, X.; Kim, S.-H.; Johnson, J. A.; Fairchild, C. R.; Lee, Francis Y. F.; Long, B. H.; Vite, G. D. Org. Lett. 2001, 3, 2396.
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Kim, S.-H.4
Johnson, J.A.5
Fairchild, C.R.6
Lee, F.Y.F.7
Long, B.H.8
Vite, G.D.9
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24
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0035825486
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Nicolaou, K. C.; Namoto, K.; Li, J.; Ritzén, A.; Ulven, T.; Shoji, M.; Zaharevitz, D.; Gussio, R.; Sackett, D. L.; Ward, R. D.; Hensler, A.; Fojo, T.; Giannakakou, P. ChemBioChem 2001, 1, 69.
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Hensler, A.11
Fojo, T.12
Giannakakou, P.13
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25
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0442266806
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0442263677
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27
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0034202896
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(a) Johnson, J. A.; Kim, S.-H.; Bifano, M.; DiMarco, J.; Fairchild, C.; Gougoutas, J.; Lee, F.; Long, B.; Tokarski, J.; Vite, G. D. Org. Lett. 2000, 2, 1537.
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29
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17744405184
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C-12 epimer of epothilone B (not shown) has been synthesized previously and shown to have a similar acitivity as epothilone B 2. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Nincovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannalakou, P.; Hamel, E. Nature 1997, 387, 268.
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Hamel, E.11
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30
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0442268284
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The improved pH stability may be due to the presence of the nitrile group as we anticipated, although the altered epoxide geometry of 24 cannot be ruled out
-
The improved pH stability may be due to the presence of the nitrile group as we anticipated, although the altered epoxide geometry of 24 cannot be ruled out.
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31
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0035955176
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Nicolaou, K. C.; Namoto, K.; Ritzen, A.; Ulven, T.; Shoji, M.; Li, J.; D'Amico, G.; Liotta, D.; French, C. T.; Wartmann, M.; Altmann, K.-H.; Giannakakou, P. J. Am. Chem. Soc. 2001, 123, 9313.
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Altmann, K.-H.11
Giannakakou, P.12
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