Expedient solid-phase synthesis of putative β-turn mimetics incorporating the i + 1, i + 2, and i + 3 sidechains

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 6961-6964

  Virgilio, Alex A ^a   Schürer, Stephan C ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01572-9     Document Type: Article

References (15)

1. 1. (a) Kitagawa, O.; Velde, D. V.; Dutta, D.; Morton, M. Takusagawa, F.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 5169-5178.
2. (b) Kahn, M. (guest editor) Symposia 50. Tetrahedron 1993, 3433-3677.
3. 2. Bach, A. C.; Espina, J. R.; Jackson, S. A.; Stouten, P. F. W.; Duke, J. L.; Mousa, S. A.; Degrado, W. F. J. Am. Chem.Soc. 1996, 118, 293-294.
4. 3. Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11580-11581.
5. 4. Virgilio, A. A.; Bray, A. M.; Ellman, J. A. Manuscript in preparation.
6. 5. Diamond, J. M.; Write, E. M. Proc. Roy. Soc. B. 1969, 172, 273-316.
7. 6. Rink, H. Tetrahedron Lett 1987, 26, 3787-3790.
8. 7. For the use of a disulfide linker for the synthesis of peptides, see: a) Mery, J.; Brugidou, J.; Derancourt, J. Peptide Res. 1992, 5, 233-240.
9. b) Mery, J.; Granier, C.; Juin, M.; Brugidou, J. Int. J. Pept. and Prot. Res. 1993, 42, 44-52.
10. 8. Brzezinska, E.; Ternay, A. L. J. Org. Chem. 1994, 59, 8239-8244.
11. 9. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70-77.
12. 10. Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J. Org. Chem. 1991, 56, 2648-2650.
13. 4NI for 12 h at reflux provides resin 8.
14. 2O solution (1 mL/μmmol of resin bound 7), which has been purged with Ar (20 min). After 8 h, the solution of acyclic turn mimetic is transferred via a filtration cannula and under Ar pressure to a flask containing ∼30 equiv of support-bound guanidine 8. After the disappearance of all of the acyclic material (<24 h), the solution is filtered to remove the resin and the filtrate is concentrated in vacuo to give 2.
15. 2: C, 59.96; H, 7.42; N, 7.36. Found: C, 59.71; H, 7.27; N, 7.17.