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Volumn 70, Issue 3, 2005, Pages 856-867

A new bicyclic dipeptide isostere with pyrrolizidinone skeleton

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEPARATION; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

EID: 13244277648     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0487653     Document Type: Article
Times cited : (39)

References (39)
  • 4
    • 0034778418 scopus 로고    scopus 로고
    • For selected reviews, see: (a) Burgess, K. Acc. Chem. Res. 2001, 34, 826-835. (b) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448. (c) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169-2187. (d) Robinson, J. A. Synlett 1999, 429-441.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 826-835
    • Burgess, K.1
  • 5
    • 0035959447 scopus 로고    scopus 로고
    • For selected reviews, see: (a) Burgess, K. Acc. Chem. Res. 2001, 34, 826-835. (b) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448. (c) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169-2187. (d) Robinson, J. A. Synlett 1999, 429-441.
    • (2001) Tetrahedron , vol.57 , pp. 7431-7448
    • Souers, A.J.1    Ellman, J.A.2
  • 6
    • 0000478078 scopus 로고
    • For selected reviews, see: (a) Burgess, K. Acc. Chem. Res. 2001, 34, 826-835. (b) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448. (c) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169-2187. (d) Robinson, J. A. Synlett 1999, 429-441.
    • (1995) Chem. Rev. , vol.95 , pp. 2169-2187
    • Schneider, J.P.1    Kelly, J.W.2
  • 7
    • 0034778418 scopus 로고    scopus 로고
    • For selected reviews, see: (a) Burgess, K. Acc. Chem. Res. 2001, 34, 826-835. (b) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448. (c) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169-2187. (d) Robinson, J. A. Synlett 1999, 429-441.
    • (1999) Synlett , pp. 429-441
    • Robinson, J.A.1
  • 10
    • 0242487836 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2003) Synthesis , pp. 2363-2367
    • Bracci, A.1    Manzoni, L.2    Scolastico, C.3
  • 11
    • 0037031636 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2002) J. Org. Chem. , vol.67 , pp. 6353-6360
    • Wang, W.1    Yang, J.2    Ying, J.3    Xiong, C.4    Zhang, J.5    Cai, C.6    Hruby, V.J.7
  • 12
    • 0035903517 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3361-3364
    • Hoffmann, T.1    Lanig, H.2    Waibel, R.3    Gmeiner, P.4
  • 13
    • 0033853117 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2000) Eur. J. Org. Chem. , pp. 2571-2581
    • Angiolini, M.1    Araneo, S.2    Belvisi, L.3    Cesarotti, E.4    Checchia, A.5    Crippa, L.6    Manzoni, L.7    Scolastico, C.8
  • 14
    • 0033853334 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2000) Eur. J. Org. Chem. , pp. 2563-2569
    • Belvisi, L.1    Bernardi, A.2    Manzoni, L.3    Potenza, D.4    Scolastico, C.5
  • 15
    • 0034616373 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2000) J. Org. Chem. , vol.65 , pp. 2163-2171
    • Gosselin, F.1    Lubell, W.D.2
  • 16
    • 0034693302 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (2000) J. Org. Chem. , vol.65 , pp. 6992-6999
    • Estiarte, M.A.1    Rubiralta, M.2    Diez, A.3    Thormann, M.4    Giralt, E.5
  • 17
    • 0030958399 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (1997) J. Org. Chem. , vol.62 , pp. 2847-2852
    • Kim, K.1    Germanas, J.P.2
  • 18
    • 0030998970 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Bracci, A.; Manzoni, L.; Scolastico, C. Synthesis 2003, 2363-2367. (b) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360. (c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571-2581. (e) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (f) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163-2171. (g) Estiarte M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (h) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847-2852. (i) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853-2860.
    • (1997) J. Org. Chem. , vol.62 , pp. 2853-2860
    • Kim, K.1    Germanas, J.P.2
  • 27
    • 13244271475 scopus 로고    scopus 로고
    • note
    • In this case the use of DMAP as base afforded better results than 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]-octane (DABCO).
  • 36
    • 13144307468 scopus 로고    scopus 로고
    • note
    • For all model compounds 18, 21, and 22, NH δ values were independent of concentration at or below 5.0 mM at 295 K.
  • 37
    • 13244256376 scopus 로고    scopus 로고
    • note
    • αH.
  • 39
    • 13244269293 scopus 로고    scopus 로고
    • note
    • The X-ray CIF files have been deposited at the Cambridge Crystallographic Data Centre and allocated with the deposition numbers CCDC 231007 for compound exo-6 and CCDC 231008 for compound (2R,7aR)-23a.


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