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24
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0042121974
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note
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3N, DMF), and HPLC analysis to confirm ≥ 97% enantiomer purity.
-
-
-
-
25
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0042623053
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note
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Transannular alkylation of the methanesulfonate i under the same conditions provided an 8:1 mixture of 9a and the alcohol derived from cleavage of the methanesulfonyl group. Attempts to cyclize the sulfonium salt ii derived from L-methionine were unsuccessful. matrix presented
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-
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26
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0033555780
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27
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0042121975
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note
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Attempted cyclization using LiHMDS (THF, -78 to 0°C, 5 h) gave only recovered 11. The use of KHMDS under the same conditions resulted in gradual conversion to the dihydrooxazinone iii. matrix presented
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-
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28
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0026747866
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(a) Kato, K.; Cox, A. D.; Hisaka, M. M.; Graham, S. M.; Buss, J. E. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 6403.
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33
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0013595306
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Boston, MA, American Chemical Society: Washington, DC, 1998; MEDI 309
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(a) Williams, T. M.; Dinsmore, C. J.; Bergman, J. M.; Hutchinson, J. H.; MacTough, S. C.; Stump, C. S.; Wei, D. D.; Zartman, C. B.; Bogusky, M. J.; Chen, I.-W.; Culberson, J. C.; Koblan, K. S.; Kohl, N. E.; Lobell, R. B.; Motzel, S. L.; Salata, J. J.; Gibbs, J. B.; Graham, S. L.; Hartman, G. D.; Oliff, A. I.; Huff, J. R. 216th National Meeting of the American Chemical Society, Boston, MA, 1998; American Chemical Society: Washington, DC, 1998; MEDI 309.
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216th National Meeting of the American Chemical Society
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Williams, T.M.1
Dinsmore, C.J.2
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Wei, D.D.7
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Chen, I.-W.10
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Koblan, K.S.12
Kohl, N.E.13
Lobell, R.B.14
Motzel, S.L.15
Salata, J.J.16
Gibbs, J.B.17
Graham, S.L.18
Hartman, G.D.19
Oliff, A.I.20
Huff, J.R.21
more..
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34
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0042623052
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(b) manuscript in preparation.
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35
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0035819989
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in press
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Dinsmore, C. J.; Bogusky, M. J.; Culberson, J. C.; Bergman, J. M.; Homnick, C. F.; Zartman, C. B.; Mosser, S. D.; Schaber, M. D.; Robinson, R. G.; Koblan, K. S.; Huber, H. E.; Graham, S. L.; Hartman, G. D.; Huff, J. R.; Williams, T. M. J. Am. Chem. Soc. 2001, 123, in press.
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Dinsmore, C.J.1
Bogusky, M.J.2
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Bergman, J.M.4
Homnick, C.F.5
Zartman, C.B.6
Mosser, S.D.7
Schaber, M.D.8
Robinson, R.G.9
Koblan, K.S.10
Huber, H.E.11
Graham, S.L.12
Hartman, G.D.13
Huff, J.R.14
Williams, T.M.15
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36
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0035952277
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Dinsmore, C. J.; Bergman, J. M.; Wei, D. D.; Zartman, C. B.; Davide, J. P.; Greenberg, I. B.; Liu, D.; O'Neill, T. J.; Gibbs, J. B.; Koblan, K. S.; Kohl, N. E.; Lobell, R. B.; Chen, I.-W.; McLoughlin, D. A.; Olah, T. V.; Graham, S. L.; Hartman, G. D.; Williams, T. M. Bioorg. Med. Chem. Lett. 2001, 11, 537.
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Liu, D.7
O'Neill, T.J.8
Gibbs, J.B.9
Koblan, K.S.10
Kohl, N.E.11
Lobell, R.B.12
Chen, I.-W.13
McLoughlin, D.A.14
Olah, T.V.15
Graham, S.L.16
Hartman, G.D.17
Williams, T.M.18
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37
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0021952325
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0022245194
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-
40
-
-
0041621099
-
-
note
-
(a) Molecular modeling: Conformations were generated using metric matrix distance geometry algorithm JG (S. Kearsley, Merck & Co., Inc., unpublished). The structures were subjected to energy minimization within Macromodel (ref 20b) using the MMFF force field.
-
-
-
-
41
-
-
84986437005
-
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(b) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
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Chang, G.6
Hendrickson, T.7
Still, W.C.8
-
42
-
-
0041621101
-
-
note
-
This interpretation is supported by computational analyses (ref 20), which revealed only moderate energy increases for the following conformational perturbations relative to lowest energy 19 (cf. Figure 2): front-to-back rotations of the imidazole, cyanophenyl rings and back-to-front rotation of the chlorophenyl ring (1.66 kcal/mol); axial - equatorial isomerization (2.94 kcal/mol).
-
-
-
-
43
-
-
0041621100
-
-
note
-
An alternative conformation of 13 with the carbonyl projected in the opposite direction relative to 19 is the enantiomer of lowest energy 13.
-
-
-
-
44
-
-
0028211246
-
-
For assay conditions, see: Graham, S. L.; deSolms, S. J.; Giuliani, E. A.; Kohl, N. E.; Mosser, S. D.; Oliff, A. I.; Pompliano, D. L.; Rands, E.; Breslin, M. J.; Deanna, A. A.; Garsky, V. M.; Scholz, T. H.; Gibbs, J. B.; Smith, R. L. J. Med. Chem. 1994, 37, 725.
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Graham, S.L.1
DeSolms, S.J.2
Giuliani, E.A.3
Kohl, N.E.4
Mosser, S.D.5
Oliff, A.I.6
Pompliano, D.L.7
Rands, E.8
Breslin, M.J.9
Deanna, A.A.10
Garsky, V.M.11
Scholz, T.H.12
Gibbs, J.B.13
Smith, R.L.14
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