Iminoiodane mediated aziridination of α-allylglycine: Access to a novel rigid arginine derivative and to the natural amino acid enduracididine

Tetrahedron

Volumn 60, Issue 28, 2004, Pages 5889-5897

  Sanière, Laurent ^a   Leman, Loïc ^a   Bourguignon, Jean Jacques ^b   Dauban, Philippe ^a   Dodd, Robert H ^a  

^a CNRS   (France)

^b Laboratoire de Pharmacochimie   (France)

Author keywords

Allylglycine; Arginine mimetic; Aziridination; Aziridine; Iminoiodane

Indexed keywords

2 TRIMETHYLSILYLETHANESULFONAMIDE; ALPHA ALLYLGLYCINE; AMINO ACID DERIVATIVE; AMINODIHYDROHISTIDINE DERIVATIVE; ARGININE DERIVATIVE; BENZENE DERIVATIVE; COPPER; ENDURACIDIDINE; GLYCINE DERIVATIVE; HISTIDINE DERIVATIVE; IMINOIODANE; IODINE DERIVATIVE; IODOSOBENZENE; PROPIONIC ACID DERIVATIVE; SULFONAMIDE; TERT BUTYL 2,4 [3 [2' N (BENZYLOXYCARBONYL)AMINOIMIDAZOLIDIN 4' YL]] 2 N (9 PHENYL 9H FLUOREN 9 YL)AMINOPROPANOATE; TERT BUTYL N (9 PHENYL 9H FLUOREN 9 YL)ALLYLGLYCINATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 2942733486     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.034     Document Type: Article

References (42)

1. Bursavich M.G., Rich D.H. J. Med. Chem. 45:2002;541-558
2. Wermuth C.G. The Practice of Medicinal Chemistry. 1996;Academic Press, London. Chapter 14
3. Lundquist J.T., Orwig K.S., Dix T.A. J. Org. Chem. 64:1999;9265-9267
4. Ulhaq S., Chinje E.C., Naylor M.A., Jaffar M., Stratford I.J., Threadgill M.D. Bioorg. Med. Chem. 7:1999;1787-1796
5. Lee Y., Marletta M.A., Martasek P., Roman L.J., Masters B.S.S., Silverman R.B. Bioorg. Med. Chem. 7:1999;1097-1104
6. Shearer B.G., Lee S., Franzmann K.W., White H.A.R., Sanders D.C.J., Kiff R.J., Garvey E.P., Furfine E.S. Bioorg. Med. Chem. Lett. 7:1997;1763-1768
7. St Laurent D.R., Balasubramanian N., Han W.T., Trehan A., Federici M.E., Meanwell N.A., Wright J.J., Seiler S.M. Bioorg. Med. Chem. 3:1995;1145-1156
8. Horii S., Kameda Y. J. Antibiot. 21:1968;665-667
9. Higashide E., Hatano K., Shibata M., Nakazawa K. J. Antibiot. 21:1968;126-137
10. Asai M., Muroi M., Sugita N., Kawashima H., Mizuno K., Miyake A. J. Antibiot. 21:1968;138-146
11. Hamada M., Kondo J., Yokoyama T., Miura K., Iinuma K., Yamamoto H., Maeda K., Takeuchi T., Umezawa H. J. Antibiot. 27:1974;81-83
12. Iinuma K., Kondo S., Maeda K., Umezawa H. J. Antibiot. 28:1975;613-615
13. Iinuma K., Kondo S., Maeda K., Umezawa H. Bull. Chem. Soc. Jpn. 50:1977;1850-1854
14. Garcia A., Vázquez M.J., Quiñoá E., Riguera R., Debitus C. J. Nat. Prod. 59:1996;782-785
15. Tsuji S., Kusumoto S., Shiba T. Chem. Lett. 1975;1281-1284
16. See references cited in: Dodd D.S., Kozikowski A.P. Tetrahedron Lett. 35:1994;977-980
17. Guillerm D., Lavrador K., Guillerm G. Synth. Commun. 25:1995;877-882
18. Dappen M.S., Pellicciari R., Natalini B., Monahan J.B., Chiorri C., Cordi A.A. J. Med. Chem. 34:1991;161-168
19. For a review of α-allyglycine chemistry, see: Rutjes F.P.J.T., Wolf L.B., Schoemaker H.E. J. Chem. Soc., Perkin Trans. 1. 2000;4197-4212
20. Evans D.A., Faul M.M., Bilodeau M.T. J. Org. Chem. 56:1991;6744-6746
21. Evans D.A., Faul M.M., Bilodeau M.T. J. Am. Chem. Soc. 116:1994;2742-2753
22. For reviews, see: (a) Dauban P., Dodd R.H. Synlett. 2003;1571-1586
23. Müller P., Fruit C. Chem. Rev. 103:2003;2905-2919
24. Dauban P., Dodd R.H. J. Org. Chem. 64:1999;5304-5307
25. White R.D., Wood J.L. Org. Lett. 3:2001;1825-1827
26. Sudau A., Münch W., Bats J.W., Nubbemeyer U. Chem. Eur. J. 7:2001;611-621
27. Schricker B., Thirring K., Berner H. Bioorg. Med. Chem. Lett. 2:1992;387-390
28. Leman L., Sanière L., Dauban P., Dodd R.H. Arkivoc. 2003;126-134
29. Lodder M., Wang B., Hecht S.M. Tetrahedron. 56:2000;9421-9429
30. Bergmeier S.C., Cobás A.A., Rapoport H. J. Org. Chem. 58:1993;2369-2376
31. Armstrong A., Brackenridge I., Jackson R.F.W., Kirk J.M. Tetrahedron Lett. 29:1988;2483-2486
32. Gosselin F., Lubell W.D. J. Org. Chem. 63:1998;7463-7471
33. Dauban P., Sanière L., Tarrade A., Dodd R.H. J. Am. Chem. Soc. 123:2001;7707-7708
34. Evans D.A., Faul M.M., Bilodeau M.T., Anderson B.A. J. Am. Chem. Soc. 115:1993;5328-5329
35. Dauban P., Dodd R.H. Tetrahedron Lett. 39:1998;5739-5742
36. 3) δ -1.8, 10.7, 22.2, 28.0, 46.1, 48.8, 56.2, 57.6, 76.3, 81.6, 120.2, 120.3, 126.0, 126.7, 127.8, 127.9, 128.0, 128.6, 129.0, 129.1, 140.1, 140.9, 141.5, 145.7, 146.9, 173.3.
37. Knouzi N., Vaultier M., Carrié R. Bull. Soc. Chim. Fr. 1985;815-819
38. Weinhardt K., Beard C.C., Dvorak C., Marx M., Patterson J., Roszkowski A., Schuler M., Unger S.H., Wagner P.J., Wallach M.B. J. Med. Chem. 27:1984;616-627
39. Su W. Synth. Commun. 26:1996;407-413
40. He H., Williamson R.T., Shen B., Graziani E.I., Yang H.Y., Sakya S.M., Petersen P.J., Carter G.T. J. Am. Chem. Soc. 124:2002;9729-9736
41. Vermeij T.A.C., Edelbroek P.M. J. Chromatography B. 716:1998;233-238
42. Farquhar D., Cherif A., Bakina E., Nelson J.A. J. Med. Chem. 41:1998;965-972