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For recent articles see: (a) Turner, S. C.; Zhai, H.; Rapoport, H. J. Org. Chem. 2000, 65, 861. (b) Cossy, J.; Tresnard, L.; Gomez Pardo, D. Synlett 2000, 3, 409. (c) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (d) Oliveira, D. J.; Coelho, F. Tetrahedron Lett. 2001, 42, 6793.
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0242427889
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Compounds 6 were obtained following the general procedure previously reported for 5 (ref 5) and 6a (ref 6). Yields: 6b (73%); 6c (55%); 6d (28%); 6e (45%); 6f (70%).
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2. The organic phase was washed with HCl (morpholine) or NaCl (alkoxydes), the solvent was evaporated, and the residue was chomatographed on silica gel with hexane/EtOAc as eluent (1:1 allowed isolation of amides and 7:3 of esters). Pyroglutamate 3 was recovered with a 3:7 mixture of solvents.
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16
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0242596087
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note
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2. The residue obtained after evaporation of the solvent was chomatographed on silica gel with hexane/EtOAc as eluent (9:1) for isolation of ketones. Auxilar 3 was recovered as indicated in ref 10.
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22
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Although lactones 10 are described as stable compounds (Romo, D.; Harrison, P. H. M.; Jenkins, S. I.; Riddoch, R. W.; Park, K.; Yang, H. W.; Zhao, C.; Eright, G. D. Bioorg. Med. Chem. 1998, 6, 1255) they seem to be prone to hydrolysis under these reaction conditions. Thus the reaction of 9c carried out in a NMR tube generates the corresponding hydroxy acid 11c in the reaction medium as we proved by following by NMR this conversion (see Supporting Information) discarding its formation in the workup.
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0242596086
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note
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2).
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0028230652
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Pedregal, C.; Ezquerra, J.; Escribano, A.; Carreño, M. C.; García Ruano, J. L. Tetrahedron Lett. 1994, 35, 2053-2056. Collado, I.; Ezquerra, J.; Vaquero, J. J.; Pedregal, C. Tetrahedron Lett. 1994, 35, 8037
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