Design, synthesis, conformational analysis and application of azabicycloalkane amino acids as constrained dipeptide mimics

Synlett

Volumn , Issue 9, 2004, Pages 1449-1471

  Belvisi, Laura ^a   Colombo, Lino ^a,b,d,e   Manzoni, Leonardo ^a,c,f,g   Potenza, Donatella ^a   Scolastico, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF PAVIA   (Italy)

^c CNR   (Italy)

^d HARVARD UNIVERSITY   (United States)

^e UNIVERSITY OF SASSARI   (Italy)

^f Harvard University ^*

^g UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Azabicycloalkane amino acids; Biological activity; Conformational analysis; Peptide secondary structure; Peptidomimetic

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKANE DERIVATIVE; AMINO ACID DERIVATIVE; ANTINEOPLASTIC AGENT; AZABICYCLOALKANE AMINO ACID; BMY 44621; BRADYKININ ANTAGONIST; CARBOXYLIC ACID DERIVATIVE; CILENGITIDE; CYCLOARGINYLGLYCYLASPARTYL DEXTRO PHENYLALANYLVALINE; DEXTRO PHENYLALANYLPROLYLARGINYLCHLOROMETHYL KETONE; ECHISTATIN; EFEGATRAN; ICATIBANT; LACTAM DERIVATIVE; PENTAPEPTIDE; PHENYLALANINE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SERINE PROTEINASE INHIBITOR; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ACYLATION; ADDITION REACTION; ALKYLATION; ALLYLATION; ANGIOGENESIS; ARTICLE; CHEMICAL BOND; CLINICAL TRIAL; CYCLIZATION; DIASTEREOISOMER; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; HORNER WADSWORTH EMMONS REACTION; HUMAN; HYDROGEN BOND; HYDROGENOLYSIS; HYDROLYSIS; HYDROPHOBICITY; INFRARED SPECTROSCOPY; MOLECULAR MODEL; MOLECULAR WEIGHT; MONTE CARLO METHOD; NONHUMAN; OXIDATION; PROTEIN PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; REDUCTION; RING CLOSING METATHESIS; STEREOCHEMISTRY; STEREOISOMERISM; THROMBOGENESIS; X RAY CRYSTALLOGRAPHY;

EID: 3943071680     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829540     Document Type: Article

References (146)

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8. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
9. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
10. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
11. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
12. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
13. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
14. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
15. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
16. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
17. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
18. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
19. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
20. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
21. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
22. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
23. Indolizidin-2-one amino acids: (a) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397. (b) Li, W.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. (c) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106. (e) Wessig, P. Tetrahedron Lett. 1999, 40, 5987. (f) Boatman, P. D.; Ogbu, C. O.; Eguchi, M.; Kim, H.-O.; Nakanishi, H.; Cao, B.; Shea, J. P.; Kahn, M. J. Med. Chem. 1999, 42, 1367. (g) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992. (h) Mulzer, J.; Schulzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289. (i) Beal, L. M.; Liu, B.; Chu, W.; Moeller, K. D. Tetrahedron 2000, 56, 10113. (j) Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 3159. (k) Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943. (l) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087. (m) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029. (n) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (o) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353. (p) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115. (q) Gardiner, J.; Abell, A. D. Tetrahedron Lett. 2003, 44, 4227.
24. Indolizidin-9-one: (a) Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463. (b) De La Figuera, N.; Rosas, I.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. J. Chem. Soc., Chem. Comm. 1994, 613. (c) Lamazzi, C.; Carbonnel, S.; Calinaud, P.; Troin, Y. Heterocycles 2003, 60, 1447. (d) Shimizu, M.; Nemoto, H.; Kakuda, H.; Takahata, H. Heterocycles 2003, 59, 245.
25. Indolizidin-9-one: (a) Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463. (b) De La Figuera, N.; Rosas, I.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. J. Chem. Soc., Chem. Comm. 1994, 613. (c) Lamazzi, C.; Carbonnel, S.; Calinaud, P.; Troin, Y. Heterocycles 2003, 60, 1447. (d) Shimizu, M.; Nemoto, H.; Kakuda, H.; Takahata, H. Heterocycles 2003, 59, 245.
26. Indolizidin-9-one: (a) Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463. (b) De La Figuera, N.; Rosas, I.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. J. Chem. Soc., Chem. Comm. 1994, 613. (c) Lamazzi, C.; Carbonnel, S.; Calinaud, P.; Troin, Y. Heterocycles 2003, 60, 1447. (d) Shimizu, M.; Nemoto, H.; Kakuda, H.; Takahata, H. Heterocycles 2003, 59, 245.
27. Indolizidin-9-one: (a) Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463. (b) De La Figuera, N.; Rosas, I.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. J. Chem. Soc., Chem. Comm. 1994, 613. (c) Lamazzi, C.; Carbonnel, S.; Calinaud, P.; Troin, Y. Heterocycles 2003, 60, 1447. (d) Shimizu, M.; Nemoto, H.; Kakuda, H.; Takahata, H. Heterocycles 2003, 59, 245.
28. Pyrroloazepinone amino acids: (a) Tremmel, P.; Geyer, A. J. Am. Chem. Soc. 2002, 124, 8548. (b) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163. (c) Geyer, A.; Moser, F. Eur. J. Org. Chem. 2000, 1113.
29. Pyrroloazepinone amino acids: (a) Tremmel, P.; Geyer, A. J. Am. Chem. Soc. 2002, 124, 8548. (b) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163. (c) Geyer, A.; Moser, F. Eur. J. Org. Chem. 2000, 1113.
30. Pyrroloazepinone amino acids: (a) Tremmel, P.; Geyer, A. J. Am. Chem. Soc. 2002, 124, 8548. (b) Gosselin, F.; Lubell, W. D. J. Org. Chem. 2000, 65, 2163. (c) Geyer, A.; Moser, F. Eur. J. Org. Chem. 2000, 1113.
31. Other examples: (a) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (b) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; Di Marco, J. D. J. Am. Chem. Soc. 1994, 116, 2348. (c) Robl, J. A.; Karanewsky, D. S.; Asaad, M. M. Tetrahedron Lett. 1995, 36, 1593. (d) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091. (e) De Lombaert, S.; Blanchard, L.; Stamford, L. B.; Sperbeck, D. M.; Grim, M. D.; Jenson, T. M.; Rodriguez, H. R. Tetrahedron Lett. 1994, 35, 7513. (f) Lombart, H. G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147. (g) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
32. Other examples: (a) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (b) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; Di Marco, J. D. J. Am. Chem. Soc. 1994, 116, 2348. (c) Robl, J. A.; Karanewsky, D. S.; Asaad, M. M. Tetrahedron Lett. 1995, 36, 1593. (d) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091. (e) De Lombaert, S.; Blanchard, L.; Stamford, L. B.; Sperbeck, D. M.; Grim, M. D.; Jenson, T. M.; Rodriguez, H. R. Tetrahedron Lett. 1994, 35, 7513. (f) Lombart, H. G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147. (g) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
33. Other examples: (a) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (b) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; Di Marco, J. D. J. Am. Chem. Soc. 1994, 116, 2348. (c) Robl, J. A.; Karanewsky, D. S.; Asaad, M. M. Tetrahedron Lett. 1995, 36, 1593. (d) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091. (e) De Lombaert, S.; Blanchard, L.; Stamford, L. B.; Sperbeck, D. M.; Grim, M. D.; Jenson, T. M.; Rodriguez, H. R. Tetrahedron Lett. 1994, 35, 7513. (f) Lombart, H. G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147. (g) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
34. Other examples: (a) Robl, J. A. Tetrahedron Lett. 1994, 35, 393. (b) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; Di Marco, J. D. J. Am. Chem. Soc. 1994, 116, 2348. (c) Robl, J. A.; Karanewsky, D. S.; Asaad, M. M. Tetrahedron Lett. 1995, 36, 1593. (d) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091. (e) De Lombaert, S.; Blanchard, L.; Stamford, L. B.; Sperbeck, D. M.; Grim, M. D.; Jenson, T. M.; Rodriguez, H. R. Tetrahedron Lett. 1994, 35, 7513. (f) Lombart, H. G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147. (g) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
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