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The acetylated pachyclavulariaenones D-F are not cytotoxic, in contrast to potent pachyclavulariaenone G having all three hydroxyls free. Susceptible cell lines were P-388 and HT-29; however, no comment is made on mechanism of action. See: Wang, G.-H.; Sheu, J.-H.; Duh, C.-Y.; Chiang, M. Y. J. Nat. Prod. 2002, 65, 1475.
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0242369947
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note
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A comparison of MM2 minimized space-filling models of pachyclavulariaenone G and (-)- FR182877 using Spartan showed considerable homology in size, shape, and disposition of polar functionality between the two natural products (Evans and Starr, unpublished).
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0242369950
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http://www.dcso.polytechnique.fr/f1-032equipe-htm
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The following investigators have indicated their efforts toward FR182877 via the Internet: Clarke (http://www.nottingham.ac.uk/~pczpac1/research-web/synthesis.html), Prunet (http://www.dcso.polytechnique.fr/f1-032equipe-htm).
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Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092. See also ref 1d for Mosher analysis data on (-)-FR182877
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(b) For a recent example, see also: Longithorone A: Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773.
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0242369951
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Complete cis-trans isomerization was observed after storing the neat unpurified reaction product for 24 h.
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0242369946
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y coefficients were 0 ± 0.05 for both the HOMO and the LUMO of the indicated atoms.
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51
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0242307045
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note
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Dihedral angle constraints were used for all PM3 calculations as follows: O(ester CO)=CI-C2=C3, 180°; C2=C3-C4=C5, 180°; C9=C10-C11=C12, 0°. Interatomic distance contraints were applied to C5-C9 and C4-C12 at distances indicated in the text for the individual experiments.
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