Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using δ-amino β-ketophosphonates and ring-closing metathesis (RCM)

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1269-1272

  Davis, Franklin A ^a   Wu, Yongzhong ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOCYCLOPENTENONE; ALKADIENE; CARBOCYCLIC NUCLEOSIDE; CYCLOPENTENONE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; METHODOLOGY; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

CYCLOPENTANES; HYDROCARBONS, CYCLIC; KETONES; MOLECULAR STRUCTURE; NUCLEOSIDES; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 2542421687     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049795v     Document Type: Article

References (40)

1. For reviews on carbocyclic nucleosides and their syntheses, see: (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229. (b) Mansour, T. S.; Storer, R. Curr. Pharm. Des. 1997, 3, 227. (c) Marquez, V. E. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, CT, 1966; Vol. 2, p 89. (d) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. (e) Borthwick, A. D.; Boggadike, K. Tetrahedron 1992, 48, 571.
2. For reviews on carbocyclic nucleosides and their syntheses, see: (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229. (b) Mansour, T. S.; Storer, R. Curr. Pharm. Des. 1997, 3, 227. (c) Marquez, V. E. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, CT, 1966; Vol. 2, p 89. (d) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. (e) Borthwick, A. D.; Boggadike, K. Tetrahedron 1992, 48, 571.
3. For reviews on carbocyclic nucleosides and their syntheses, see: (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229. (b) Mansour, T. S.; Storer, R. Curr. Pharm. Des. 1997, 3, 227. (c) Marquez, V. E. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, CT, 1966; Vol. 2, p 89. (d) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. (e) Borthwick, A. D.; Boggadike, K. Tetrahedron 1992, 48, 571.
4. For reviews on carbocyclic nucleosides and their syntheses, see: (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229. (b) Mansour, T. S.; Storer, R. Curr. Pharm. Des. 1997, 3, 227. (c) Marquez, V. E. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, CT, 1966; Vol. 2, p 89. (d) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. (e) Borthwick, A. D.; Boggadike, K. Tetrahedron 1992, 48, 571.
5. For reviews on carbocyclic nucleosides and their syntheses, see: (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229. (b) Mansour, T. S.; Storer, R. Curr. Pharm. Des. 1997, 3, 227. (c) Marquez, V. E. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, CT, 1966; Vol. 2, p 89. (d) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. (e) Borthwick, A. D.; Boggadike, K. Tetrahedron 1992, 48, 571.
6. For related methods for the synthesis of 2, see: (a) Schaudt, M.; Blechert, S. J. Org. Chem. 2003, 68, 2913. (b) O'Brien, P.; Towers, T. D.; Voith, M. Tetrahedron Lett. 1998, 39, 8175.
7. For related methods for the synthesis of 2, see: (a) Schaudt, M.; Blechert, S. J. Org. Chem. 2003, 68, 2913. (b) O'Brien, P.; Towers, T. D.; Voith, M. Tetrahedron Lett. 1998, 39, 8175.
8. Trost, B. M.; Stenkamp, D.; Pulley, S. R. Chem. Eur. J. 1995, 1, 568.
9. Ghosh, A.; Ritter, A. R.; Miller, M. J. J. Org. Chem. 1995, 60, 5808.
10. Mineno, T.; Miller, M. J. J. Org. Chem. 2003, 68, 6591.
11. Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719.
12. Vogt, P. F.; Hansel, J.-G.; Miller, M. J. Tetrahedron Lett. 1997, 38, 2803.
13. Mulvihill, M. J.; Gage, J. L.; Miller, M. J. J. Org. Chem. 1998, 63, 3357.
14. Ramesh, N. G.; Klunder, A. J. H.; Zwanenburg, B. J. Org. Chem. 1999, 64, 3635.
15. Bakkeren, F. J. A. D.; Ramesh, N. G.; de Goot, D.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1996, 37, 8003.
16. For leading references to sulfinimine derived chiral building blocks, see: Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
17. For reviews and leading references on ring-closing metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342. (c) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693. (d) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
18. For reviews and leading references on ring-closing metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342. (c) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693. (d) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
19. For reviews and leading references on ring-closing metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342. (c) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693. (d) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
20. For reviews and leading references on ring-closing metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342. (c) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693. (d) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
21. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
22. Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310.
23. (a) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253 and references therein.
24. (b) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606.
25. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
26. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
27. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
28. For a review, see: McKenna, C. E.; Kashemirov, B. A. Top. Curr. Chem. 2002, 220, 201.
29. (a) Baldwin, J. E.; Adlington, R. M.; Russell, A. T.; Smith, M. L. Tetrahedron 1995, 51, 4733.
30. (b) Lee, H. K.; Kim, E.-K.; Pak, C. S. Tetrahedron Lett. 2002, 43, 9641.
31. Rudisill, E. E.; Whitten, J. P. Synthesis 1994, 85.
32. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, T.; Zhou, P.; Carroll, P. J. J. Org. Chem, 1997, 62, 2555.
33. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037.
34. Roy, A.; Schneller, S. W. J. Org. Chem. 2003, 68, 9269.
35. Davis, F. A.; Prasad, K. R.; Nolt, B. M.; Wu, Y. Org. Lett. 2003, 5, 925.
36. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
37. (b) Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677.
38. (c) Krikstolaityte, S.; Hammer, K.; Undheim, K. Tetrahedron Lett. 1998, 39, 7595.
39. (d) Paquette, L. A.; Efremov, I. J. Am. Chem. Soc. 2001, 123, 4492.
40. Wu, Y.; Woster, P. M. J. Med. Chem,. 1992, 35, 3196.