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(a) For other applications of 3-amino-2-piperidones as pseudo-peptides, see: M. A. Estiarte, M. Rubiralta, A. Diez, M. Thormann and E. Giralt, J. Org. Chem., 2000, 65, 6992-6999:
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For a review on the syntheses of 3-aminopiperidones in solution, see: (a) C. Flamant-Robin, Q. Wang and N. A. Sasaki, Tetrahedron Lett., 2001, 42, 8483-8484; (b) J. Aubé, Advances in Amino Acid Mimetics and Peptidomimetics, JAY Press Inc, 1997, vol. 1, p. 193.
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0035955843
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JAY Press Inc
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For a review on the syntheses of 3-aminopiperidones in solution, see: (a) C. Flamant-Robin, Q. Wang and N. A. Sasaki, Tetrahedron Lett., 2001, 42, 8483-8484; (b) J. Aubé, Advances in Amino Acid Mimetics and Peptidomimetics, JAY Press Inc, 1997, vol. 1, p. 193.
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Aubé, J.1
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2942743495
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The only precedent of a lactamisation on solid phase was reported as a side-reaction in the context of an intramolecular amino acid coupling: Y. Lee and R. B. Silverman, Synthesis, 1999, 495-1499.
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22
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0031033427
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The resin was functionalised as an active carbonate according to: J. Alsina, C. Chiva, M. Ortiz, F. Rabanal, E. Giralt and F. Albericio, Tetrahedron Lett., 1997, 38, 883-886.
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0032582863
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2942743013
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International Symposium, 7th. Southampton, United Kingdom, Sept. 18-22, Ed. R. Epton, Mayflower Worldwide Ltd, Kingswinford, UK
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For the procedure and preliminary results see: M. Garcia, M. Rubiralta, A. Diez, H. Ryder, E. Lozoya and V. Segarra, in Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries: Peptides, Proteins and Nucleic Acids-Small Molecule Organic Chemical Diversity, Collected Papers, International Symposium, 7th. Southampton, United Kingdom, Sept. 18-22, 2002, Ed. R. Epton, Mayflower Worldwide Ltd, Kingswinford, UK, p. 205.
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26
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45949130729
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Alloc-cyclo-Orn was synthesized in solution by cyclodehydration of L-ornithine according to: A. Bladé-Font, Tetrahedron Lett., 1980, 21, 2443-2446 and subsequent protection of the α-amino with an allyloxycarbonyl group following the protocol by E. J. Corey and J. W. Suggs, J. Org. Chem., 1973, 38, 3223-3224. The sample was not optically pure.
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Bladé-Font, A.1
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27
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0000470828
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The sample was not optically pure
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Alloc-cyclo-Orn was synthesized in solution by cyclodehydration of L-ornithine according to: A. Bladé-Font, Tetrahedron Lett., 1980, 21, 2443-2446 and subsequent protection of the α-amino with an allyloxycarbonyl group following the protocol by E. J. Corey and J. W. Suggs, J. Org. Chem., 1973, 38, 3223-3224. The sample was not optically pure.
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Corey, E.J.1
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-
28
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2942728185
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note
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Compound 28 was characterised by the NMR and HPLC data of the product cleaved from an aliquot of the resin. The purity determined by HPLC was higher than 95%.
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29
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0030932342
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(a) C. G. Boojamra, K. M. Burow, L. A. Thompson and J. A. Ellman, J. Org. Chem., 1997, 62, 1240-1256;
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(b) F. X. Woolard, J. Paetsch and J. A. Ellman, J. Org. Chem., 1997, 62, 6102-6103.
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36
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M. del Fresno, J. Alsina, M. Royo, G. Barany and F. Albericic, Tetrahedron Lett., 1998, 39, 2639-2642.
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37
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2942713515
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note
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-1.
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38
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2942758266
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note
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The manipulation of the resulting dimer was delicate, mainly because of its size and polarity.
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39
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2942728641
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note
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We expected to obtain three stereoisomers for compounds 7 prepared from racemic lactams: the racemic RR and SS forms and the meso epimer RS. However, we could not detect the diastereomeric mixture by standard methods such as NMR and analytical HPLC. Since the compounds turned out not to be sufficiently active, we did not pursue this issue.
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