A concise and efficient synthesis of isoindolin-1-ones. New synthetic approach to the polycyclic framework of vitedoamine A

Tetrahedron

Volumn 63, Issue 12, 2007, Pages 2664-2669

  Lamblin, Marc ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a UNIV LILLE   (France)

Author keywords

Iminodicarboxylates; Isoindolinones; Mitsunobu reaction; Parham procedure

Indexed keywords

2 IODO 3 METHOXY N,N DIMETHOXYCARBONYLBENZYLAMINE; 2 IODO 3,4 METHYLENEDIOXY N,N DIMETHOXYCARBONYLBENZYLAMINE; 2 IODO 5 METHOXY N,N DIMETHOXYCARBONYLBENZYLAMINE; 2,3 DIHYDRO 1H BENZ[E]ISOINDOL 1 ONE; 2,3 DIHYDRO 5 METHOXY 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 7 BENZYLOXY 6 METHOXY 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 7 METHOXY 1H ISOINDOL 1 ONE; 3 BENZYLOXY 2 IODO 4 METHOXY N,N DIMETHOXYCARBONYLBENZYLAMINE; 6,7 DIHYDRO 1,3 8H DIOXOLO[4,5 E]ISOINDOL 8 ONE; AMINE; BENZYLAMINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; N,N DIMETHOXYCARBONYL (2 IODONAPHTHALEN 1 YL)METHYLAMINE; UNCLASSIFIED DRUG; VITEDOAMINE A;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IODINATION; PRIORITY JOURNAL;

EID: 33846926120     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.021     Document Type: Article

References (60)

1. Stájer G., and Csende F. Curr. Org. Chem. 9 (2005) 1277-1286
2. Sánchez-Sánchez C., Pérez-Inestrosa E., García-Segura R., and Suau R. Tetrahedron 58 (2002) 7267-7274
3. Abramovitch R.A., Shinkai I., Mavunkel B.J., More K.M., O'Connor S., Ooi G.H., Pennington W.T., Srinivasan P.C., and Stowers J.R. Tetrahedron 52 (1996) 3339-3354
4. Heaney H., and Shuhaibar K.F. Synlett (1995) 47-48
5. Pendrak I., Barney S., Wittrock R., Lambert D.M., and Kingsbury W.D. J. Org. Chem. 59 (1994) 2623-2625
6. De Clercq E. J. Med. Chem. 38 (1995) 2491-2517
7. Nannini G., Giraldi P.N., Molgora G., Biasoli G., Spinelli F., Logemann W., Dradi E., Zanni G., Buttinoni A., and Tommasini R. Arzneim. Forsch. 23 (1973) 1090-1100
8. Hisamitsu (Pharmaceutical Co., Inc.). Jpn. Kokai Tokkyo Koho JP 149257, 1980;
9. Chem. Abstr. 94 (1981) 174879
10. Schmahl H.J., Dencker L., Plum C., Chahoud I., and Nau H. Arch. Toxicol. 11 (1996) 749-756
11. Shinji C., Maeda S., Imai K., Yoshida M., Hashimoto Y., and Miyachi H. Bioorg. Med. Chem. 14 (2006) 7625-7651
12. Fajardo V., Elango V., Cassels B.K., and Shamma M. Tetrahedron Lett. 23 (1982) 39-42
13. Rodriguez G., Cid M.M., Saa C., Castedo L., and Dominguez D. J. Org. Chem. 61 (1996) 2780-2782
14. Daïch A., Marchalin S., Pigeon P., and Decroix B. Tetrahedron Lett. 39 (1998) 9187-9190
15. Späth E., and Lintner J. Chem. Ber. 69B (1936) 2727-2731
16. Barrios I., Camps P., Comes-Franchini M., Muñoz-Torrero D., Ricci A., and Sanchez L. Tetrahedron 59 (2003) 1971-1979
17. Horii Z.-I., Iwata C., and Tamura Y. J. Org. Chem. 26 (1961) 2273-2276
18. Pendergast W., Dickerson S.H., Dev I.K., Ferone R., Duch D.S., and Smith G.K. J. Med. Chem. 37 (1994) 838-844
19. Taylor E.C., Jennings L.D., Mao Z., Hu B., Jun J.-G., and Zhou P. J. Org. Chem. 62 (1997) 5392-5403
20. Wang H., and Ganesan A. Tetrahedron Lett. 39 (1998) 9097-9098
21. Orito K., Miyazawa M., Nakamura T., Horibata A., Ushito H., Nagasaki H., Yuguchi M., Yamashita S., Yamazaki T., and Tokuda M. J. Org. Chem. 71 (2006) 5951-5958
22. Hoarau C., Couture A., Deniau E., and Grandclaudon P. Synthesis (2000) 655-660
23. Tsuritani T., Kii S., Akao A., Sato K., Nonoyama N., Mase T., and Yasuda N. Synlett (2006) 801-803
24. Mori M., Chiba K., and Ban Y. J. Org. Chem. 43 (1978) 1684-1687
25. Campbell J.B., Dedinas R.F., and Trumbower-Walsh S.A. J. Org. Chem. 61 (1996) 6205-6211
26. Luzzio F.A., and Zacherl D.P. Tetrahedron Lett. 39 (1998) 2285-2288
27. Grigg R., Zhang L., Collard S., and Keep A. Tetrahedron Lett. 44 (2003) 6979-6982
28. Wahab Khan Md., and Masud Reza A.F.G. Tetrahedron 61 (2005) 11204-11210
29. Anderson P.S., Christy M.E., Colton C.D., and Shepard K.L. J. Org. Chem. 43 (1978) 3719-3723
30. Guo Z., and Schultz A.G. J. Org. Chem. 66 (2001) 2154-2157
31. Couture A., Deniau E., Ionescu D., and Grandclaudon P. Tetrahedron Lett. 39 (1998) 2319-2320
32. Fains O., and Vernon J.M. Tetrahedron Lett. 38 (1997) 8265-8266
33. Moreau A., Couture A., Deniau E., and Grandclaudon P. Eur. J. Org. Chem. (2005) 3437-3442
34. Lamblin M., Couture A., Deniau E., and Grandclaudon P. Tetrahedron 62 (2006) 2917-2921
35. Moreau A., Couture A., Deniau E., Grandclaudon P., and Lebrun S. Tetrahedron 60 (2004) 6169-6176
36. Moreau A., Couture A., Deniau E., Grandclaudon P., and Lebrun S. Org. Biomol. Chem. 3 (2005) 2305-2309
37. Moreau A., Lorion M., Couture A., Deniau E., and Grandclaudon P. J. Org. Chem. 71 (2006) 3303-3305
38. Reviews:
39. Parham W.E., and Bradsher C.K. Acc. Chem. Res. 15 (1982) 300-305
40. Wakefield B.J. The Chemistry of Organolithium Compounds. 2nd ed. (1990), Pergamon, New York, NY
41. Gray M., Tinkl M., and Snieckus V. In: Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II Vol. 11 (1995), Pergamon, Exeter 66-92
42. Ardeo A., Collado M.I., Osante I., Ruiz J., Sotomayor N., and Lete E. In: Atanassi O., and Spinelli D. (Eds). Targets in Heterocyclic Systems Vol. 5 (2001), Italian Society of Chemistry, Rome 393-418
43. Clayden J. Organolithiums: Selectivity for Synthesis (2002), Elsevier Science, Oxford
44. Mealy M.J., and Bailey W.F. J. Organomet. Chem. 646 (2002) 59-67
45. Sotomayor N., and Lete E. Curr. Org. Chem. 7 (2003) 275-300
46. Nájera C., Sansano J.M., and Yus M. Tetrahedron 59 (2003) 9255-9303
47. De la Fuente M.C., and Dominguez D. Tetrahedron 60 (2004) 10019-10028
48. Giger, R. K. A. Swiss Pat. CH 648300, 1985;
49. Chem. Abstr. 103 (1985) 71188
50. Agami C., and Couty F. Tetrahedron 58 (2002) 2701-2724
51. Rico R., and Bermejo F. Tetrahedron Lett. 37 (1996) 5809-5812
52. Li W.-R., Lin S.T., Hsu N.-M., and Chern M.-S. J. Org. Chem. 67 (2002) 4702-4706
53. Ono M., Nishida Y., Masuoko C., Li J.-C., Okawa M., Ikeda T., and Nohara T. J. Nat. Prod. 67 (2004) 2073-2075
54. Snieckus V. Chem. Rev. 90 (1990) 879-933
55. Piers E., Harrison C.L., and Zetina-Rocha C. Org. Lett. 3 (2001) 3245-3247
56. Ruiz J., Ardeo A., Ignacio R., Sotomayor N., and Lete E. Tetrahedron 61 (2005) 3311-3324
57. Liang P.-H., Liu J.P., Hsin L.-W., and Cheng C.-Y. Tetrahedron 60 (2004) 11655-11660
58. Cornejo J.J., Ghodsi S., Johnson R.D., Woodling R., and Rickborn B. J. Org. Chem. 48 (1983) 3869-3876
59. Tomita M., Minami S., and Uyeo S. J. Chem. Soc. C (1969) 183-188
60. Klemm L.H., McGuire T.M., and Gopinath K.W. J. Org. Chem. 41 (1976) 2571-2579