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(a) Maibaum, J.; Rasetti, V.; Rüeger, H.; Cohen, N.C.; Göschke, R.; Mah, R.; Rahuel, J.; Grütter, M.G.; Cumin, F.; Wood, J.M. In: Medicinal Chemistry: Today and Tomorrow. Proceedings of the AFMC International Medicinal Chemistry Symposium, Tokyo, 3-8 September 1995; Mikio Yamazaki (Ed.), Blackwell Science UK, 1997, p.155-162.
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0343269844
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Poster abstract
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Seattle (USA); August 8-17th
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16
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0342834977
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note
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1 site than the corresponding C7(R)-stereoisomer, in agreement with the in vitro binding data for the ethyl homologues 12, 13.
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17
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0027934039
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An alternative synthesis of the prototype 8-phenyI-2(R),7(R)-dimethyl model analogue of 10 and 11 has been recently disclosed: Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697.
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Hanessian, S.1
Raghavan, S.2
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18
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0343705428
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note
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All new compounds have been characterized at least by high resolution 1 H-NMR and/or FAB mass spectrometry.
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21
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0342834974
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note
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The precursors of 8a-f were prepared similarly as 5b,c from the mono-substituted benzylbromides and the corresponding (R)configured N-acyl Evans auxiliaries. (S)-8c was prepared from 3-isovaleroyl-4(S)-benzyl-oxazolidin-2-one ((S)-27c).
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23
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0000925727
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Racemisation during cleavage of the oxazolidinone auxiliary by transesterification using the more basic lithium benzyl oxide has been described previously: Trimble, L.A.; Vederas, J.C. J. Am. Chem. Soc. 1986, 108, 6397.
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Vederas, J.C.2
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Schöllkopf, U.1
Groth, U.2
Deng, Ch.3
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26
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0343705427
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In our hands, n-butylacrylamide proved to be more stable than methyacrylamide on storage at lower temperature, probably due to a reduced susceptibility for polymerisation (cf. Fitt, J.; Gschwend, H.W. J. Org. Chem. 1980, 45, 4257). The compound could be kept for several months at < -10 °C without signs of decomposition.
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Fitt, J.1
Gschwend, H.W.2
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27
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0342400254
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note
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6) for the 4(S)-vs. 4(R)-isomers. In all cases, the 4(R)-diastereomers corresponding to 7c appeared to be more polar by t.l.c..
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28
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33845281684
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3 [see: Takaya, H.; Noyori, R. et al, J. Am. Chem. Soc. 1987, 109, 1596] to give the desired 2(R)-methyl isomers (H. Rüeger, personal communication).
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Takaya, H.1
Noyori, R.2
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29
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0343269824
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note
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The regioisomeric inhibitor 22 was obtained accordingly starting from 4-(tert-butyl)-2-hydroxy-benzoic acid.
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30
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0026487085
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Weber, A.E.; Steiner, M.G.; Krieter, P.H.; Colletti, A.E.; Tata, J.R.; Halgren, T.A.; Ball, R.G.; Doyle, J.J.; Schorn, T.W.; Stearns, R.A.; Miller, R.R.; Siegl, P.K.S.; Greenlee, W.J.; Patchett, A.A. J.Med.Chem. 1992, 35, 3755.
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Ball, R.G.7
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0026323860
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For a recent review: Rahuel, J.; Priestle, J.P.; Grütter, M.G. J. Struct. Biology 1991, 107, 227.
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0023238799
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Foundling, S.I.; Cooper, J.; Watson, F.E.; Cleasby, A.; Pearl, L.H.; Sibanda, B.L.; Hemmings, A.; Wood, S.P.; Blundell, T.L.; Valler, M.J.; Norey, C.G.; Kay, J.; Boger, J.; Dunn, B.M.; Leckie, B.J.; Jones, D.M.; Atrash, B.; Hallett, A.; Szelke, M. Nature 1987, 327, 349.
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Pearl, L.H.5
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Hemmings, A.7
Wood, S.P.8
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Valler, M.J.10
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Jones, D.M.16
Atrash, B.17
Hallett, A.18
Szelke, M.19
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33
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0342400252
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note
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3 extended dipeptide isosteres in our laboratories [Ref. 5].
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