Synthesis of β-hydroxy-β-(fluoronitrophenyl)alanines: Vital components in the assembly of biologically active cyclic peptides

Organic Letters

Volumn 1, Issue 2, 1999, Pages 295-297

  Hutton, Craig A ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; CYCLOPEPTIDE; DRUG DERIVATIVE; NITROBENZENE DERIVATIVE;

ARTICLE; STEREOISOMERISM; SYNTHESIS;

ALANINE; NITROBENZENES; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 0033614881     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906054     Document Type: Article

References (24)

1. (a) Feng, Y.; Wang, Z.; Jin, S.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 10768.
2. (b) Raeppel, S.; Raeppel, F.; Suffert, J. Synlett 1998, 794.
3. (c) Zhu, J. Synlett 1997, 133.
4. (a) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700.
5. (b) Boger, D. L.; Beresis, R. T.; Loiseleur, O.; Wu, J. H.; Castle, S. L. Bioorg. Med. Chem. Lett. 1998, 8, 721.
6. (c) Rama Rao, A. V. Pure Appl. Chem. 1998, 70, 391.
7. (d) Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721.
8. (e) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433.
9. (f) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535.
10. (a) Bigot, A.; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753.
11. (b) Boger, D. L.; Zhou, J.; Borzilleri, R. M.; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054.
12. (c) Boger, D. L.; Borzilleri, R. M. Bioorg. Med. Chem. Lett. 1995, 5, 1187.
13. Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7741.
14. (a) East, S. P.; Shao, F.; Williams, L.; Joullie, M. M. Tetrahedron 1998, 54, 13371.
15. (b) Laib, T.; Zhu, J. Tetrahedron Lett. 1998, 39, 283.
16. (a) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251.
17. (b) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 39, 7081.
18. Kimura, T. K.; Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734.
19. Evans (ref 2a) reports that the stannous triflate mediated aldol reaction of 6 with 4-fluoro-3-nitrobenzaldehyde proceeds to give the corresponding threo-β-hydroxy amino acid derivative with 95:5 diastereoselectivity, whereas Zhu et al. (ref 6b) report that the identical reaction gives only moderate diastereoselectivity and chemical yield. (equation presented)
20. Mackay, M. F.; Donkelaar, A. V.; Culvenor, C. C. V. J. Chem. Soc., Chem. Commun. 1986, 1219.
21. Hutton, C. A. Tetrahedron Lett. 1997, 38, 5899.
22. Easton, C. J.; Hutton, C. A.; Roselt, P. D.; Tiekink, E. R. T. Tetrahedron 1994, 50, 7327.
23. Vergne, C.; Bois-Choussy, M.; Ouazzani, J.; Beugelmans, R.; Zhu, J. Tetrahedron: Asymmetry 1997, 8, 391.
24. Easton, C. J.; Hutton, C. A.; Merrett, M. C.; Tiekink, E. R. T. Tetrahedron 1996, 52, 7025.