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For biological studies, see: (a) ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243; (b) Schreiber, S. L.; Chen, J.; Hung, D. T. Chem. Biol. 1996, 3, 287; (c) Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1997, 52, 613; (d) Balachandran, R.; ter Haar, E.; Welsh, M. J.; Grant, S. G.; Day, B. W. Anti-Cancer Drugs 1998, 9, 67; (e) Martello, M. A.; McDaid, H. M.; Regl, D. L.; Yang, C. H.; Meng, D.; Pettus, T. R. R.; Kaufman, M. D.; Arimoto, H.; Danishefsky, S. J.; Smith, A. B., III; Horwitz, S. B. Clin. Cancer Res. 2000, 6, 1978; (f) Kar, S.; Florence, G. J.; Paterson, I.; Amos, L. A. FEBS Letters 2003, 539, 34.
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For biological studies, see: (a) ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243; (b) Schreiber, S. L.; Chen, J.; Hung, D. T. Chem. Biol. 1996, 3, 287; (c) Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1997, 52, 613; (d) Balachandran, R.; ter Haar, E.; Welsh, M. J.; Grant, S. G.; Day, B. W. Anti-Cancer Drugs 1998, 9, 67; (e) Martello, M. A.; McDaid, H. M.; Regl, D. L.; Yang, C. H.; Meng, D.; Pettus, T. R. R.; Kaufman, M. D.; Arimoto, H.; Danishefsky, S. J.; Smith, A. B., III; Horwitz, S. B. Clin. Cancer Res. 2000, 6, 1978; (f) Kar, S.; Florence, G. J.; Paterson, I.; Amos, L. A. FEBS Letters 2003, 539, 34.
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For biological studies, see: (a) ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243; (b) Schreiber, S. L.; Chen, J.; Hung, D. T. Chem. Biol. 1996, 3, 287; (c) Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1997, 52, 613; (d) Balachandran, R.; ter Haar, E.; Welsh, M. J.; Grant, S. G.; Day, B. W. Anti-Cancer Drugs 1998, 9, 67; (e) Martello, M. A.; McDaid, H. M.; Regl, D. L.; Yang, C. H.; Meng, D.; Pettus, T. R. R.; Kaufman, M. D.; Arimoto, H.; Danishefsky, S. J.; Smith, A. B., III; Horwitz, S. B. Clin. Cancer Res. 2000, 6, 1978; (f) Kar, S.; Florence, G. J.; Paterson, I.; Amos, L. A. FEBS Letters 2003, 539, 34.
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Pettus, T.R.R.6
Kaufman, M.D.7
Arimoto, H.8
Danishefsky, S.J.9
Smith A.B. III10
Horwitz, S.B.11
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For biological studies, see: (a) ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243; (b) Schreiber, S. L.; Chen, J.; Hung, D. T. Chem. Biol. 1996, 3, 287; (c) Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1997, 52, 613; (d) Balachandran, R.; ter Haar, E.; Welsh, M. J.; Grant, S. G.; Day, B. W. Anti-Cancer Drugs 1998, 9, 67; (e) Martello, M. A.; McDaid, H. M.; Regl, D. L.; Yang, C. H.; Meng, D.; Pettus, T. R. R.; Kaufman, M. D.; Arimoto, H.; Danishefsky, S. J.; Smith, A. B., III; Horwitz, S. B. Clin. Cancer Res. 2000, 6, 1978; (f) Kar, S.; Florence, G. J.; Paterson, I.; Amos, L. A. FEBS Letters 2003, 539, 34.
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Kar, S.1
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85030940835
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Boston, MA, August 18-22, 2002; 236-MEDI, Part 2; ACS, Washington, DC
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Kinder, F. R.; Bair, K. W.; Chen, W. C.; Florence, G.; Francavilla, C.; Geng, P.; Gunasekera, S.; Lassota, P. T.; Longley, R. E.; Palermo, M. G.; Paterson, I.; Pomponi, S.; Ramsay, T. M.; Rogers, L.; Sabio, M.; Sereinig, N.; Sorenson, E.; Wang, R. M.; Wright, A.; Guo, Q. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA, August 18-22, 2002; 236-MEDI, Part 2; ACS, Washington, DC, 2002.
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Lassota, P.T.8
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Palermo, M.G.10
Paterson, I.11
Pomponi, S.12
Ramsay, T.M.13
Rogers, L.14
Sabio, M.15
Sereinig, N.16
Sorenson, E.17
Wang, R.M.18
Wright, A.19
Guo, Q.20
more..
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24
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84986437005
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-
A 20,000 step Monte Carlo search was performed for the structures 1, 3 and 4 using the AMBER force field, together with the generalised Born/surface area (CB/SA) water solvent model. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comp. Chem. 1990, 11, 440.
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25
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0034829880
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-
In each case, we found several discrete families of low energy conformations, as anticipated from the results of Snyder and co-workers. For conformational studies on discodermolide, see: (a) Monteagudo, E.; Cicero, D. O.; Cornett, B.; Myles D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 123, 6929; (b) Smith, A. B., III; La Marche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695.
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Snyder, J.P.5
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26
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0035826325
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In each case, we found several discrete families of low energy conformations, as anticipated from the results of Snyder and co-workers. For conformational studies on discodermolide, see: (a) Monteagudo, E.; Cicero, D. O.; Cornett, B.; Myles D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 123, 6929; (b) Smith, A. B., III; La Marche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695.
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Smith A.B. III1
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0000194961
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Paterson I., Goodman J.M., Lister M.A., Schumann R.C., McClure C.K., Norcross R.D. Tetrahedron. 46:1990;4663.
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Norcross, R.D.6
-
33
-
-
85030943989
-
-
note
-
+ 614.3669, found 614.3671.
-
-
-
-
34
-
-
85030943823
-
-
On acid treatment of 19, rapid deprotection of the two TBS groups and the TES group was accomplished in 80% yield in 1 h. In contrast, the TBS ether at C3 on the δ-lactone of discodermolide requires prolonged treatment with acid (2-3 days) for complete removal and this was found to be incompatible with the oxetane group
-
On acid treatment of 19, rapid deprotection of the two TBS groups and the TES group was accomplished in 80% yield in 1 h. In contrast, the TBS ether at C3 on the δ-lactone of discodermolide requires prolonged treatment with acid (2-3 days) for complete removal and this was found to be incompatible with the oxetane group.
-
-
-
-
35
-
-
85030949316
-
-
note
-
+ 615.3509, found 615.3516.
-
-
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