A practical synthesis of (-)-kainic acid

Synthesis

Volumn , Issue 23, 2011, Pages 3848-3858

  Takita, Satoshi ^a   Yokoshima, Satoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Curtius rearrangement; iodolactone; kainoids; stereoselective alkylation; total synthesis

Indexed keywords

CURTIUS REARRANGEMENT; IODOLACTONE; KAINOIDS; STEREO-SELECTIVE; TOTAL SYNTHESIS;

ALKYLATION; CARBOXYLIC ACIDS; CYANIDES; STEREOSELECTIVITY;

AMINO ACIDS;

1 METHYL 4 (PROP 1 EN 2 YL) 7 OXOBICYCLO[4.1.0]HEPTAN 2 ONE; 2 [2 (IODOMETHYL) 2 METHYL 5 OXOTETRAHYDROFURAN 3 YL]ACETALDEHYDE; 2 [2 (IODOMETHYL) 2 METHYL 5 OXOTETRAHYDROFURAN 3 YL]ACETIC ACID; ALLYL 3 [2 (TERT BUTOXY) 2 OXOETHYL]2 CYANO 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; CARBOXYLIC ACID; CARVONE; IODOLACTONE; KAINIC ACID; LACTONE; METHYL 2 [CHLORO[(2,6 DICHLOROPHENYL)IMINO]METHYL] 3 (2 METHOXY 2 OXOETHYL) 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; METHYL 2 CYANO 3 (2 METHOXY 2 OXOETHYL) 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; METHYL 3 [2 (TERT BUTOXY) 2 OXOETHYL] 2 (5 METHYLFURAN 2 YL) 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; METHYL 3 [2 (TERT BUTOXY) 2 OXOETHYL] 2 CYANO 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; METHYL 3 [2 (TERT BUTOXY) 2 OXOETHYL] 2 METHOXY 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; METHYL [[2 (IODOMETHYL) 2 METHYL 5 OXOTETRAHYDROFURA 3 YL]METHYL]CARBAMIC ACID; TERT BUTYL 2 [5 (IODOMETHYL) 4 [[(METHOXYCARBON YL)AMINO]METHYL] 5 METHYL 2 OXOTETRAHYDROFURAN 3 YL]ACETIC ACID; TERT BUTYL 3 [2 (TERT BUTOXY) 2 OXOETHYL] 2 CYANO 4 (PROP 1 EN 2 YL)PYRROLIDINE 1 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; HYDROLYSIS; STEREOCHEMISTRY;

EID: 81855170180     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289570     Document Type: Article

References (72)

1. Murakami S, Takemoto T, Shimizu Z, J. Pharm. Soc. Jpn. 1953 73 1026
2. Impellizzeri G, Mangiafico S, Oriente G, Piatelli M, Sciuto S, Fattorusso E, Magno S, Santacroce C, Sica D, Phytochemistry 1975 14 1549
3. Balansard G, Gayte-Sorbier A, Cavalli C, Timond-David P, Gasquent M, Ann. Pharm. Fr. 1982 40 527
4. Balansard G, Pellegrini M, Cavalli C, Timon-David P, Gasquet M, Boudon G, Ann. Pharm. Fr. 1983 41 77
5. Maloney M G., Nat. Prod. Rep. 1998 15 205
6. Maloney M G., Nat. Prod. Rep. 1999 16 485
7. Maloney M G., Nat. Prod. Rep. 2002 19 597
8. Parsons A F., Tetrahedron 1996 52 4149
9. Hashimoto K, Shirahama H, J. Synth. Org. Chem. Jpn. 1989 47 212
10. Nitta I, Watase H, Tomiie Y, Nature (London) 1958 181 761
11. Hashimoto K, Shirahama H, Trends Org. Chem. 1991 2 1
12. Cantrell B E., Zimmerman D M., Monn J A., Kamboj R K., Hoo K H., Tizzano J P., Pullar I A., Farrell L N., Bleakman D J., J. Med. Chem. 1996 39 3617
13. MacGeer E G., Olney J W., MacGeer P L., Kainic Acid as a Tool in Neurobiology Raven New York 1978
14. Sperk G, Prog. Neurobiol. (Oxford) 1994 42 1
15. Coyle J T., Schwarcz R, Nature (London) 1976 263 244
16. For recent reviews
17. For selected examples, see:, Ueno Y, Tanaka K, Ueyanagi J, Nawa H, Sanno Y, Honjo M, Nakamori R, Sugawa T, Uchibayashi M, Osugi K, Tatsuoka S, Proc. Jpn. Acad. 1957 33 53
18. Oppolzer W, Thirring K, J. Am. Chem. Soc. 1982 104 4978
19. Takano S, Iwabuchi Y, Ogasawara K, J. Chem. Soc., Chem. Commun. 1988 1204
20. Takano S, Sugihara T, Satoh S, Ogasawara K, J. Am. Chem. Soc. 1988 110 6467
21. Baldwin J E., Moloney M G., Parsons A F., Tetrahedron 1990 46 7263
22. Jeong N, Yoo S.-E, Lee S J., Lee S H., Chung Y K., Tetrahedron Lett. 1991 32 2137
23. Barco A, Benetti S, Pollimi G P., Spalluto G, Zanirato V, J. Chem. Soc., Chem. Commun. 1991 390
24. Cooper J, Knight D W., Gallagher P T., J. Chem. Soc., Perkin Trans. 1 1992 553
25. Takano S, Inomata K, Ogasawara K, J. Chem. Soc., Chem. Commun. 1992 169
26. Hatakeyama S, Sugawara K, Takano S, J. Chem. Soc., Chem. Commun. 1993 125
27. Yoo S.-E, Lee S H., [nl] J. Org. Chem. 1994 59 6968
28. Hanessian S, Ninkovic S, J. Org. Chem. 1996 61 5418
29. Nakada Y, Sugahara T, Ogasawara K, Tetrahedron Lett. 1997 38 857
30. Bachi M D., Melman A, J. Org. Chem. 1997 62 1896
31. Miyata O, Ozawa Y, Ninomiya I, Naito T, Synlett 1997 275
32. Rubio A, Ezquerra J, Escribano A, Remuinan M J., Vaquero J J., Tetrahedron Lett. 1998 39 2171
33. Cossy J, Cases M, Pardo D G., Tetrahedron Lett. 1999 55 6153
34. Campbell A D., Raynham T M., Taylor R J. K., Chem. Commun. 1999 245
35. Chevliakov M V., Montgomery J, J. Am. Chem. Soc. 1999 121 11139
36. Miyata O, Ozawa Y, Ninomiya I, Naito T, Tetrahedron 2000 56 6199
37. Nakagawa H, Sugahara T, Ogasawara K, Org. Lett. 2000 2 3181
38. Xia Q, Ganem B, Org. Lett. 2001 3 485
39. Hirasawa H, Taniguchi T, Ogasawara K, Tetrahedron Lett. 2001 42 7587
40. Clayden J, Menet C J., Tchabanenko K, Tetrahedron 2002 58 4727
41. Martínez M M., Hoppe D, Eur. J. Org. Chem. 2005 7 1427
42. Anderson J C., OLoughlin J M. A., Tornos J A., Org. Biomol. Chem. 2005 3 2741
43. (aa), Trost B M., Rudd M T., J. Am. Chem. Soc. 2005 127 4763
44. (ab), Scott M E., Lautens M, Org. Lett. 2005 7 3045
45. (ac), Poisson J.-F, Orellana A, Greene A E., J. Org. Chem. 2005 70 10860
46. (ad), Morita Y, Tokuyama H, Fukuyama T, Org. Lett. 2005 7 4337
47. (ae), Sushil S K., Orellana A, Greene A E., Poisson J.-F, Org. Lett. 2006 8 5665
48. (af), Jung Y C., Yoon C H., Turos E, Yoo K S., Jung K W., J. Org. Chem. 2007 72 10114
49. (ag), Chalker J M., Deng A Y. K., Cohen T, Org. Lett. 2007 9 3825
50. (ah), Sakaguchi H, Tokuyama H, Fukuyama T, Org. Lett. 2007 9 1635
51. (ai), Tomooka K, Akiyama T, Man P, Suzuki M, Tetrahedron Lett. 2008 49 6327
52. (aj), Sakaguchi H, Tokuyama H, Fukuyama T, Org. Lett. 2008 10 1711
53. (ak), Farwick A, Helmchen G, Org. Lett. 2010 12 1108
54. (al), Kitamoto K, Sampei M, Nakayama Y, Sato T, Chida N, Org. Lett. 2010 12 5756
55. (am), Farwick A, Engelhart J U., Tverskoy O, Welter C, Umlauf Q A., Rominger F, Kerr W J., Helmchen G, Adv. Synth. Catal. 2011 353 349
56. (an), Kamon K, Irifune Y, Tanaka T, Yoshimitsu T, Org. Lett. 2011 13 2674
57. Tremblay J.-F, Chem. Eng. News 2000 78 (3) 14
58. Tremblay J.-F, Chem. Eng. News 2000 78 (6) 31
59. Tremblay J.-F, Chem. Eng. News 2001 79 (29) 19
60. Takita S, Yokoshima S, Fukuyama T, Org. Lett. 2011 13 2068
61. Lavallée J.-F, Spino C, Ruel R, Hogan K T., Deslongchamps P, Can. J. Chem. 1992 70 1406
62. González M A., Ghosh S, Rivas F, Fischer D, Theodorakis E A., Tetrahedron Lett. 2004 45 5039
63. Mori K, Fukumatsu K, Liebigs Ann. Chem. 1992 489
64. Kraus G A., Taschner M J., J. Org. Chem. 1980 45 1175
65. Kraus G A., Roth B, J. Org. Chem. 1980 45 4825
66. Bal B S., Childers W E., Pinnick H W., Tetrahedron 1981 37 2091
67. Shioiri T, Ninomiya K, Yamada S, J. Am. Chem. Soc. 1972 94 6203
68. Chamberlin A R., Dezube M, Tetrahedron Lett. 1982 23 3055
69. Chamberlin A R., Dezube M, Reich S H., Sall D J., J. Am. Chem. Soc. 1989 111 6247
70. Yamada S, Kasai Y, Shioiri T, Tetrahedron Lett. 1973 14 1595
71. Shono T, Matsumura Y, Tsubata K, Tetrahedron Lett. 1981 22 2411
72. Guirado A, Zapata A, Gómez J L., Trahalón L, Gálvez J, Tetrahedron 1999 55 9631