ꢀ
ꢀ
E. Jimenez-Gonzalez et al. / Tetrahedron 68 (2012) 9842e9852
9852
12. (a) El Mahdi, O.; Lavergne, J.-P.; Martinez, J.; Viallefont, Ph.; Riche, C. Synth.
52.37 (CH2Ph), 56.36 (
*
CH), 83.95 (C(CH3)3), 127.92 (ArC), 128.14
CH),
Commun. 1997, 27, 3539e3545; (b) El Mahdi, O.; Lavergne, J.-P.; Martinez, J.;
Viallefont, Ph.; Essassi, E. M.; Riche, C. Eur. J. Org. Chem. 2000, 251e255; (c)
Giovannoni, J.; Subra, G.; Amblard, M.; Martinez, J. Tetrahedron Lett. 2001, 42,
5389e5392.
(ArC), 128.95 (ArC), 136.47 (Cipso), 152.73 (CON), 170.08 (CO
*
173.22 (COCH2). IR (KBr, cmꢁ1): nmax 2980, 1715, 1630, 1251, 1151,
697. MS (20 eV): m/z 332 (Mþ), 321, 274, 232, 191, 160, 141, 124, 106,
91, 57, 41. Elemental Anal. Calcd for C18H24O4N2: C, 65.04; H, 7.28; N,
8.43; found: C, 65.02; H, 7.39; N, 8.77.
€
13. (a) Bieraugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org.
€
Biomol. Chem. 2003, 1, 1830e1832; (b) David, O.; Meester, W. J. N.; Bieraugel, H.;
Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Angew. Chem., Int. Ed.
2003, 42, 4373e4375; (c) Rutters, J. P. A.; Verdonk, Y.; de Vries, R.; Ingemann, S.;
Hiemstra, H.; Levacher, V.; van Maarseveen, J. H. Chem. Commun. 2012, 48,
8084e8086.
Acknowledgements
ꢀ
~
~
~
14. (a) Escalante, J.; Gonzalez-Tototzin, M. A.; Avina, J.; Munoz-Muniz, O.; Juaristi, E.
We are grateful to CONACyT for financial support via the ANUIES-
ECOS Mexico-France program (project no. M07-S02). E.J.G. is
grateful to CONACyT for her doctoral fellowship. We are also in-
debted to Professor Jaime Escalante (CIQ-UAEMor, Mexico) and Dr.
Yamir Bandala (CINVESTAV-IPN, Mexico) for helpful suggestions.
~
Tetrahedron 2001, 57, 1883e1890; (b) Juaristi, E.; Avina, J. Pure Appl. Chem. 2005,
77, 1235e1241.
ꢀ
15. (a) Jensen, K. J.; Alsina, J.; Songster, M. F.; Vagner, J.; Albericio, F.; Barany, G. J.
Am. Chem. Soc. 1998, 120, 5441e5452; (b) Gordon, E. M.; Barrett, R. W.; Dower,
W. J.; Fdor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385e1401; (c) For
a recent, authoritative review, see: El-Faham, A.; Albericio, F. Chem. Rev. 2011,
111, 6557e6602.
ꢀ
16. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Pedone, C.; Isernia,
C.; Pavone, V. Biopolymers 1996, 38, 683e691.
Supplementary data
ꢂ
17. Crystal data for (ꢀ)-3c: C25H40N2O5, triclinic, space group P-1, a¼11.264 A, b¼11.
3
ꢂ
¼75.93ꢂ,
b
¼82.87ꢂ,
g
¼62.47 , V¼1318.9 A , crystal size: 0.
ꢂ
ꢂ
ꢂ
375 A, c¼11.969 A,
a
6ꢃ0.5ꢃ0.4 mm3, R1¼0.0518, (wR2¼0.1311). CCDC 849453 contains the sup-
plementary crystallographic data for this structure. These data can be obtained
free of charge from The Cambridge Crystallographic Data Center via http://
Supplementary data associated with this article can be found in
References and notes
18. (a) Demmer, O.; Frank, A. O.; Kessler, H. Design of Cyclic Peptides In Peptide and
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20. Crystal data for (R)-5c: C16H22N2O2, monoclinic, space group P21, a¼10.
0757(5) A, b¼7.3140(3) A, c¼10.2174(5) A,
a
¼90ꢂ,
b
¼102.285(3)ꢂ,
g
¼90ꢂ,
ꢂ
ꢂ
ꢂ
ꢂ
3
3
V¼735.7 A , crystal size: 0.62ꢃ0.5ꢃ0.25 mm , R1¼0.0381, (wR2¼0.0959). CCDC
849454 contains the supplementary crystallographic data for this structure.
These data can be obtained free of charge from The Cambridge Crystallographic
ꢂ
21. Crystal data for (R)-5f: C18H18N2O2, triclinic, space group P-1, a¼6.9251(3) A,
ꢂ
ꢂ
b¼8.1821(3) A, c¼14.1725(5) A,
a
¼103.682(2)ꢂ,
b
¼92.338(2)ꢂ,
g
¼97.882(3)ꢂ,
5. (a) Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512e523; (b) Smith, D. D.;
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3
ꢂ
3
V¼770.6 A , crystal size: 0.12ꢃ0.25ꢃ0.55 mm , R1¼0.0518, (wR2¼0.1311). CCDC
849455 contains the supplementary crystallographic data for this paper. These
data can be obtained free of charge from The Cambridge Crystallographic Data
ꢀ
Marugan, J. J.; Schubert, C.; Koblish, H. K.; Lu, T.; Zhao, S.; Player, M. R.; Mar-
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b-Amino Acids in Natural
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b
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Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.;
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X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.;
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Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg,
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ꢁ
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€
9. (a)Muller-Hartwieg,J.C.D.;Akyel,K.G.;Zimmermann,J.J. Pept. Sci. 2003,9,187e199;
ˇ
€
(b) Fader, L. D.; Bethell, R.; Bonneau, P.; Bos, M.; Bousquet, Y.; Cordingley, M. G.;
Coulombe, R.; Deroy, P.; Faucher, A.-M.; Gagnon, A.; Goudreau, N.; Grand-Maõtre, C.;
Guse, I.; Hucke, O.; Kawai, S. H.; Lacoste, J.-E.; Landry, S.; Lemke, C. T.; Malenfant, E.;
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ꢀ
25. Crystal data for (ꢀ)-6a: C18H24N2O4, monoclinic, space group P2(1)/c, a¼14.
Tetrahedron Lett. 1996, 37, 8081e8084; (d) Juaristi, E.; Leon-Romo, J. L.;
¼90ꢂ,
b
¼98.7136(10)ꢂ,
g
¼90ꢂ,
ꢂ
ꢂ
ꢂ
ꢀ
0998(4) A, b¼6.2825(2) A, c¼20.6293(7) A,
a
Ramírez-Quiros, Y. J. Org. Chem. 1999, 64, 2914e2918; (e) Lack, O.; Martin, R. E.
V¼1806.293(98) A , crystal size: 0.67ꢃ0.25ꢃ0.15 mm3, R1¼0.0617, (wR2¼0.
1388). CCDC 849456 contains the supplementary crystallographic data for this
structure. These data can be obtained free of charge from The Crystallographic
3
ꢂ
€
Tetrahedron Lett. 2005, 46, 8207e8211; (f) Suli-Vargha, H.; Schlosser, G.; Ilas, J. J.
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~
Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammatter, E.;
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