Synthesis of (S,Z)-3-[(1H-indol-3-yl)methylidene]hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one: an alternative, enaminone based, route to unsaturated cyclodipeptides

Tetrahedron

Volumn 64, Issue 12, 2008, Pages 2801-2815

  Wagger, Jernej ^a   Grošelj, Uroš ^a   Meden, Anton ^a   Svete, Jurij ^a   Stanovnik, Branko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

3 (Indol 3 yl)methylidene piperazine 2,5 dione; Copper(I) catalyzed coupling; Cyclodipeptides; Enaminones; Indoles; Natural products

Indexed keywords

2 METHYLINDOLE; 2 PHENYLINDOLE DERIVATIVE; 3 [(1H INDOL 3 YL)METHYLIDENE]HEXAHYDROPYRROLO[1,2 A]PYRAZIN 4(1H)ONE; 3 [(1H INDOL 3 YL)METHYLIDENE]HEXAHYDROPYRROLO[1,2 A]PYRAZINE 1,4 DIONE; 3 [(2 METHYL 1H INDOL 3 YL)METHYLIDENE]HEXAHYDROPYRROLO[1,2 A]PYRAZINE 1,4 DIONE; 3 [(2 PHENYL 1H INDOL 3 YL)METHYLIDENE]HEXAHYDROPYRROLO[1,2 A]PYRAZINE 1,4 DIONE; 3 [(DIMETHYLAMINO)METHYLIDENE]HEXAHYDROPYRROLO[1,2 A]PYRAZINE 1,4 DIONE; ACETIC ACID ETHYL ESTER; ACRYLIC ACID DERIVATIVE; AMIDE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER; CYCLOPEPTIDE; DIPEPTIDE DERIVATIVE; ETHYL 2 BROMO 3 (2 METHYL 1H INDOL 3 YL)PROPENOATE; ETHYL 2 BROMO 3 (2 PHENYL 1H INDOL 3 YL)PROPENOATE; ETHYL 3 (2 METHYL 1H INDOL 3 YL)PROPENOATE; ETHYL 3 (2 PHENYL 1H INDOL 3 YL)PROPENOATE; ETHYL 3 (DIMETHYLAMINO)PROPENOATE; INDOLE DERIVATIVE; N BOC PROLINAMIDE; PYRAZINE DERIVATIVE; TERT BUTYL 3 [2 [1 (TERT BUTOXYCARBONYL)PYROLIDINE 2 CARBOXAMIDO] 3 ETHOXY 3 OXOPROP 1 ENYL] 2 METHYL 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 3 [2 [1 (TERT BUTOXYCARBONYL)PYROLIDINE 2 CARBOXAMIDO] 3 ETHOXY 3 OXOPROP 1 ENYL] 2 PHENYL 1H INDOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RACEMIZATION; SYNTHESIS;

EID: 39149087336     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.045     Document Type: Article

References (52)

1. Kawasaki T., and Higuchi K. Nat. Prod. Rep. 22 (2005) 761-793
2. Cui C.B., Kakeya H., and Osada H. J. Antibiot. 49 (1996) 832-835
3. Li Y., Li X., Kang J.S., Choi H.D., and Son B.W. J. Antibiot. 57 (2004) 337-340
4. Ravikanth V., Redy L.N., Ramesh P., Rao T.P., Diwan T.P., Khar A., and Venkateswarlu Y. Phytochemistry 58 (2001) 1263-1266
5. Hibino S., and Chosi T. Nat. Prod. Rep. 19 (2001) 148-180
6. Sjögren A., Johnson A.-L., Hedner E., Dahlström M., Göransson U., Shirani H., Bergman, and Jonsson P.R. Peptides 27 (2006) 2058-2064
7. Sölter S., Dieckmann R., Blumberg M., and Francke W. Tetrahedron Lett. 43 (2002) 3385-3386
8. Sørensen D., Larsen O.T., Christophersen C., Nielsen P.H., and Anthoni U. Phytochemistry 51 (1999) 1181-1183
9. Jin S., Wessig P., and Liebscher J. J. Org. Chem. 66 (2001) 3984-3997
10. Domingo L.R., Zaragozá R.J., and Williams R.M. J. Org. Chem. 68 (2003) 2895-2902
11. Boyd S.A. J. Org. Chem. 52 (1987) 1790-1794
12. Couladouros E.A., and Magos A.D. Mol. Divers. 9 (2005) 111-121
13. Aoki T., Kamisuki S., Kimoto M., Ohnishi K., Takakusagi Y., Kuramochi K., Takeda Y., Nakazaki A., Kuroiwa K., Ohuchi T., Sugawara F., Arai T., and Kobayashi S. Synlett (2006) 677-680
14. Avendano C., Cabezas N., de la Cuesta E., and Gonzales J.F. ARKIVOC ix (2005) 30-38
15. Humphrey J.M., and Chamberlin R.A. Chem. Rev. 97 (1997) 2243-2266
16. Yonezawa Y., Shin C., Ono Y., and Yoshimura J. Bull. Chem. Soc. Jpn. 53 (1980) 2905-2909
17. Moriya T., Yoneda N., Myoshi M., and Matsumoto K. J. Org. Chem. 47 (1982) 94-98
18. Liebscher J., and Jin S. Chem. Soc. Rev. 28 (1999) 251-259
19. Wagger J., Grošelj U., Meden A., Svete J., and Stanovnik B. Helv. Chim. Acta 89 (2006) 240-248
20. Stanovnik B., and Svete J. Chem. Rev. 104 (2004) 2433-2480
21. Stanovnik B., and Svete J. Synlett (2000) 1077-1091
22. Selič L., Jakše R., Lampič K., Golič L., Golič Grdadolnik S., and Stanovnik B. Helv. Chim. Acta 83 (2000) 2802-2811
23. Selič L., and Stanovnik B. Tetrahedron 57 (2001) 3159-3164
24. Selič L., Rečnik S., and Stanovnik B. Heterocycles 58 (2002) 577-585
25. Jakše R., Krošelj V., Rečnik S., Soršak G., Svete J., Stanovnik B., and Golič Grdadolnik S. Z. Naturforsch. B57 (2002) 453-459
26. Jakše R., Svete J., Stanovnik B., and Golič A. Tetrahedron 60 (2004) 4601-4608
27. Jakše R., Bevk D., Golič A., Svete J., and Stanovnik B. Z. Naturforsch. B61 (2006) 413-419
28. Jakše R., Rečnik S., Svete J., Golobič A., Golobič L., and Stanovnik B. Tetrahedron 57 (2001) 8395-8403
29. Časar Z., Bevk D., Svete J., and Stanovnik B. Tetrahedron 61 (2005) 7508-7519
30. Stanovnik B., and Svete J. Mini-Rev. Org. Chem. 2 (2005) 211-224
31. For review on Bredereck's reagent see:. Abdulla R.F., and Brinkmeyer R.S. Tetrahedron 35 (1979) 1675-1735
32. Wagger J., Grošelj U., Meden A., Stanovnik B., and Svete J. Tetrahedron: Asymmetry 18 (2007) 464-475
33. Bocchi V., and Palla G. Synthesis 12 (1982) 1096-1097
34. Gribble G., and Li J.J. Palladium in Heterocyclic Chemistry;. Tetrahedron Organic Chemistry Series Vol. 20, (2000), Elsevier Science, Oxford pp 75-83
35. Basel Y., and Hassner A. Synthesis (2001) 550-552
36. Jacquemard U., Bénéteau V., Lefoix M., Routier S., Méreour J.Y., and Coudert G. Tetrahedron 60 (2004) 10039-10047
37. Jiang L., Job G.E., Klapars A., and Buchwald S.L. Org. Lett. 5 (2003) 3667-3669
38. Richard D.J., Schiavi B., and Joullié M.M. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 11971-11976
39. Bartoli G., Bosco M., Dalpozzo R., Giuliani A., Marcantoni E., Mecozzi T., Sambri L., and Torregiani E. J. Org. Chem. 67 (2002) 9111-9114
40. Vendeville S., Goossens F., Debreu-Fontaine M.A., Landry V., Davioud-Charvet E., Grellier P., Scharpe S., and Sergheraert C. Bioorg. Med. Chem. 10 (2002) 1719-1729
41. Pozdnev V. Tetrahedron Lett. 36 (1995) 7115-7118
42. Nozaki S., and Muramatsu I. Bull. Chem. Soc. Jpn. 61 (1988) 2647-2648
43. Clark J.H. Chem. Rev. 80 (1980) 429-452
44. Lee G.H., Youn I.K., Choi E.B., Lee H.K., Yon G.H., Yang H.C., and Pak C.S. Curr. Org. Chem. 8 (2004) 1263-1287
45. Masui Y., Chino N., and Sakakibara S. Bull. Chem. Soc. Jpn. 53 (1980) 464-468
46. A related approach for enantiomeric excess determination, using enantiomerically pure 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one, has been reported recently. Bergmann H., Grosch B., Sitterberg S., and Bach T. J. Org. Chem. 69 (2004) 970-973
47. Collect Software (1998), Nonius, BV, Delft, The Netherlands
48. Otwinowski Z., and Minor W. Methods Enzymol. 276 (1997) 307-326
49. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., and Spagna R. J. Appl. Crystallogr. 32 (1999) 115-119
50. Hall S.R., King G.S.D., and Stewart J.M. The Xtal3.4 User's Manual (1995), University of Western Australia, Lamb, Perth
51. Burnett, M. N.; Johnson, C.K. ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996.
52. Wang H., and Robertson B.E. In: Wilson A.J.C. (Ed). Structure and Statistics in Crystallography (1985), Adenine, New York, NY