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The term "peptoid" is used as describing a "peptide-like compound" ("-oid" from the Old Greek ετδoΣ "picture"). It was originally restricted to oligomers of N-substituted glycines: R. J. Simon, R. S. Kania, R. N. Zuckermann, V. D. Huebner, D. A. Jewell, S. Banville, S. Ng, L. Wang, S. Rosenberg, C. K. Marlowe, D. C. Spellmeyer, R. Tan, A. D. Frankel, D. V. Santi, F. E. Cohen, P. A. Bartlett, Proc. Natl. Acad Sci. USA 1992, 89, 9367-9371.
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3
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0038571206
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note
-
+ complexes remain unchanged even in solutions of 1,10-phenanthroline and can be cleaved photochemically only under non-physiological conditions (see ref.[16b]).
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4
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5
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0019481598
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More than 25 bastadins have been isolated from marine sponges: [5a] R. Kazlauskas, R. O. Lidgard, P. T. Murphy, R. J. Wells, J. F. Blount, Aust. J. Chem. 1981, 34, 765-786. [5b] Y. Venkateswarlu, U. Venkatesham, M. Rama Rao, J. Nat. Prod. 1999, 62, 893-894 and references cited therein; total syntheses: [5c] S. Nishiyama, T. Suzuki, S. Yamamura, Chem. Lett. 1982, 11, 1851-1852. [5d] Z. Guo, K. Machiya, G. M. Salamonczyk, C. J. Sih, J. Org. Chem. 1998, 63, 4269-4276. [5e] E. A. Couladouros, V. I. Moutsos, Tetrahedron Lett. 1999, 40, 7027-7030.
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Kazlauskas, R.1
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Wells, R.J.4
Blount, J.F.5
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6
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0033025818
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and references cited therein total syntheses
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More than 25 bastadins have been isolated from marine sponges: [5a] R. Kazlauskas, R. O. Lidgard, P. T. Murphy, R. J. Wells, J. F. Blount, Aust. J. Chem. 1981, 34, 765-786. [5b] Y. Venkateswarlu, U. Venkatesham, M. Rama Rao, J. Nat. Prod. 1999, 62, 893-894 and references cited therein; total syntheses: [5c] S. Nishiyama, T. Suzuki, S. Yamamura, Chem. Lett. 1982, 11, 1851-1852. [5d] Z. Guo, K. Machiya, G. M. Salamonczyk, C. J. Sih, J. Org. Chem. 1998, 63, 4269-4276. [5e] E. A. Couladouros, V. I. Moutsos, Tetrahedron Lett. 1999, 40, 7027-7030.
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Venkateswarlu, Y.1
Venkatesham, U.2
Rama Rao, M.3
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7
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0001946505
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More than 25 bastadins have been isolated from marine sponges: [5a] R. Kazlauskas, R. O. Lidgard, P. T. Murphy, R. J. Wells, J. F. Blount, Aust. J. Chem. 1981, 34, 765-786. [5b] Y. Venkateswarlu, U. Venkatesham, M. Rama Rao, J. Nat. Prod. 1999, 62, 893-894 and references cited therein; total syntheses: [5c] S. Nishiyama, T. Suzuki, S. Yamamura, Chem. Lett. 1982, 11, 1851-1852. [5d] Z. Guo, K. Machiya, G. M. Salamonczyk, C. J. Sih, J. Org. Chem. 1998, 63, 4269-4276. [5e] E. A. Couladouros, V. I. Moutsos, Tetrahedron Lett. 1999, 40, 7027-7030.
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Nishiyama, S.1
Suzuki, T.2
Yamamura, S.3
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0032569073
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More than 25 bastadins have been isolated from marine sponges: [5a] R. Kazlauskas, R. O. Lidgard, P. T. Murphy, R. J. Wells, J. F. Blount, Aust. J. Chem. 1981, 34, 765-786. [5b] Y. Venkateswarlu, U. Venkatesham, M. Rama Rao, J. Nat. Prod. 1999, 62, 893-894 and references cited therein; total syntheses: [5c] S. Nishiyama, T. Suzuki, S. Yamamura, Chem. Lett. 1982, 11, 1851-1852. [5d] Z. Guo, K. Machiya, G. M. Salamonczyk, C. J. Sih, J. Org. Chem. 1998, 63, 4269-4276. [5e] E. A. Couladouros, V. I. Moutsos, Tetrahedron Lett. 1999, 40, 7027-7030.
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Machiya, K.2
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0033578740
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More than 25 bastadins have been isolated from marine sponges: [5a] R. Kazlauskas, R. O. Lidgard, P. T. Murphy, R. J. Wells, J. F. Blount, Aust. J. Chem. 1981, 34, 765-786. [5b] Y. Venkateswarlu, U. Venkatesham, M. Rama Rao, J. Nat. Prod. 1999, 62, 893-894 and references cited therein; total syntheses: [5c] S. Nishiyama, T. Suzuki, S. Yamamura, Chem. Lett. 1982, 11, 1851-1852. [5d] Z. Guo, K. Machiya, G. M. Salamonczyk, C. J. Sih, J. Org. Chem. 1998, 63, 4269-4276. [5e] E. A. Couladouros, V. I. Moutsos, Tetrahedron Lett. 1999, 40, 7027-7030.
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Moutsos, V.I.2
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37049077940
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+-complexed methoxybenzenes undergo nucleophilic aliphatic substitution at the methyl carbon atom on prolonged treatment with a large excess of KOtBu: [14a] F. Moulines, L. Djakovitch, M.-H. Delville, F. Robert, P. Gouzerh, D. Astruc, J. Chem. Soc. Chem. Commun. 1995, 463-464. [14b] V. Sartor, S. Nlate, J.-L. Fillaut, L. Djakovitch, F. Moulines, V. Marvaud, F. Neveu, J.-C. Blais, J.-F. Létard, D. Astruc, New J. Chem. 2000, 24, 351-370 and references cited therein.
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27
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0033932089
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and references cited therein
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+-complexed methoxybenzenes undergo nucleophilic aliphatic substitution at the methyl carbon atom on prolonged treatment with a large excess of KOtBu: [14a] F. Moulines, L. Djakovitch, M.-H. Delville, F. Robert, P. Gouzerh, D. Astruc, J. Chem. Soc. Chem. Commun. 1995, 463-464. [14b] V. Sartor, S. Nlate, J.-L. Fillaut, L. Djakovitch, F. Moulines, V. Marvaud, F. Neveu, J.-C. Blais, J.-F. Létard, D. Astruc, New J. Chem. 2000, 24, 351-370 and references cited therein.
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Astruc, D.10
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28
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0038571203
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note
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The introduction of the benzyl group worked best by employing benzyl chloride and NaH. Use of benzyl bromide leads to the formation of the benzyl ester as a side product.
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