Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones

Tetrahedron

Volumn 59, Issue 6, 2003, Pages 755-765

  Onitsuka, Satoaki ^a   Nishino, Hiroshi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

3 acetyl 1 aryl 2 pentene 1,4 diones; BF3 catalyzed cyclization; Bis(furyl)methanes; Diels Alder reaction; Furfuryl carbocation intermediate; Polyfunctionalized furans; Tetrasubstituted furans; Trisubstituted furans

Indexed keywords

3 ACETYL 2 PENTENE 1,4 DIONE; ACETYLACETONE; ALCOHOL; CHEMICAL COMPOUND; CYCLOPENTADIENE DERIVATIVE; FURAN DERIVATIVE; GLYOXAL DERIVATIVE; HYDROCHLORIC ACID; METHANE; PENTENONE; PHOSPHINE DERIVATIVE; SOLVENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; OXYGENATION; PRIORITY JOURNAL; SYNTHESIS; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

BETULACEAE; STAPHYLOCOCCUS PHAGE 3A;

EID: 0037415515     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01597-1     Document Type: Article

References (84)

1. (a) Dean F.A. Naturally Occurring Oxygen Ring Compounds; Butterworths: London, 1963.
2. (b) Nakanishi K., Goto T., Ito S., Natori S., Nozoe S. Natural Products Chemistry. Vols. 1-3:1974;Kodansha, Tokyo. 1975, 1983
3. (c) Dean F.M. Katritzky A.R. Advances in Heterocyclic Chemistry. Vol. 30:1982;167-238 Academic, New York,
4. (d) Dean F.M. Katritzky A.R. Advances in Heterocyclic Chemistry. Vol. 31:1983;237-344 Academic, New York.
5. (a) Dunlop A.P., Peters F.N. The Furans. 1953;Reinhold, New York
6. (b) Bosshard P., Eugster C.H. Katritzky A.R., Boulton A.J. Advances in Heterocyclic Chemistry. Vol. 7:1966;377-488 Academic, New York
7. (c) Livingstone R. Coffey S. 2nd ed. Rodd's Chemistry of Carbon Compounds. Vol. IV:1973;83-217 Elsevier, Amsterdam. Part A, Chapter 2.
8. (a) Corey E.J., Cheng X.-M. The Logic of Chemical Synthesis. 1989;Wiley, New York
9. (b) Nicolaou K.C., Sorensen E.J. Classics in Total Synthesis. 1996;VCH, Weinheim.
10. (a) Benassi R. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. Vol. 2:1996;259-295 Pergamon, Oxford
11. (b) Heaney H., Ahn J.S. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. Vol. 2:1996;297-357 Pergamon, Oxford
12. (c) Friedrichsen W. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. Vol. 2:1996;351-393 Pergamon, Oxford
13. (d) Keay B.A., Dibble P.W. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. Vol. 2:1996;395-436 Pergamon, Oxford
14. (e) Trost B.M., Fleming I. Comprehensive Organic Synthesis. 1991;Pergamon, Oxford.
15. (a) Nishino H. Bull. Chem. Soc. Jpn. 58:1985;1922-1927
16. (b) Nishino H., Yoshida T., Kurosawa K. Bull. Chem. Soc. Jpn. 64:1991;1097-1107
17. (c) Qian C.-Y., Hirose J., Nishino H., Kurosawa K. J. Heterocycl. Chem. 31:1994;1219-1227
18. (d) Nishino H., Nguyen V.-H., Yoshinaga S., Kurosawa K. J. Org. Chem. 61:1996;8264-8271
19. (e) Ouyang J., Nishino H., Kurosawa K. J. Heterocycl. Chem. 34:1997;81-86
20. (f) Nguyen V.-H., Nishino H., Kurosawa K. Synthesis. 1997;899-908
21. (g) Kajikawa S., Noiri Y., Shudo H., Nishino H., Kuroswa K. Synthesis. 1998;1457-1462.
22. (a) Avery T.D., Taylor D.K., Tiekink E.R.T. J. Org. Chem. 65:2000;5531-5546
23. (b) Adam W., Balci M., Kiliç H. J. Org. Chem. 65:2000;5926-5931.
24. (a) Adam W., Rodriguez A. J. Am. Chem. Soc. 102:1980;404-406
25. (b) Graziano M.L., Iesce M.R., Scarpati R. J. Chem. Soc., Perkin Trans. 1. 1980;1955-1959
26. (c) Graziano M.L., Iesce M.R., Carli B., Scarpati R. Synthesis. 1982;736-738
27. (d) Graziano M.L., Iesce M.R., Carli B., Scarpati R. Synthesis. 1983;125-126
28. (e) Graziano M.L., Iesce M.R., Chiosi S., Scarpati R. J. Chem. Soc., Perkin Trans. 1. 1983;2071-2074
29. (f) Graziano M.L., Iesce M.R. Synthesis. 1984;64-66
30. (g) Graziano M.L., Iesce M.R., Scarpati R. Synthesis. 1984;66-68
31. (h) Iesce M.R., Cermola F., Graziano M.L., Scarpati R. J. Chem. Soc., Perkin Trans. 1. 1994;147-152
32. (i) Iesce M.R., Cermola F., Guitto A., Giordano F. J. Chem. Soc., Perkin Trans. 1. 1999;475-478.
33. (a) Onitsuka S., Nishino H., Kurosawa K. Heterocycl. Commun. 6:2000;529-532
34. (b) Onitsuka S., Nishino H., Kurosawa K. Tetrahedron. 57:2001;6003-6009.
35. Onitsuka S., Nishino H., Kurosawa K. Tetrahedron Lett. 41:2000;3149-3152.
36. (a) Alickmann D., Fröhlich R., Maulitz A.H., Würthwein E.-U. Eur. J. Org. Chem. 2002;1523-1537
37. (b) Lutz R.E., Stuart A.H. J. Am. Chem. Soc. 59:1937;2316-2321
38. (c) Nowlin G. J. Am. Chem. Soc. 72:1950;5754-5756.
39. Ishihara K. Yamamoto H. Lewis Acids in Organic Synthesis. 2000;89-190 Wiley/VCH, Weinheim.
40. (a) Howes P.D., Stirling C.J.M. Organic Synthesis. Collect. Vol. 6:1988;Wiley, New York. pp 31-38
41. (b) Hendrickson J.B., Rees R., Templeton J.F. J. Am. Chem. Soc. 86:1964;107-111
42. (c) Davies H.M.L., Cantrell W.R. Jr., Romines K.R., Baum J.S. Org. Synth. 70:1991;93
43. (d) Marshall J.A., Robinson E.D. J. Org. Chem. 55:1990;3450-3451
44. (e) Garst M.E., Spencer T.A. J. Am. Chem. Soc. 95:1973;250-252.
45. (a) Gabriele B., Salerno G., Lauria E. J. Org. Chem. 64:1999;7687-7692
46. (b) Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Org. Chem. 64:1999;7693-7699
47. (c) Jeevanandam A., Narkunan K., Ling Y.-C. J. Org. Chem. 66:2001;6014-6020
48. (d) Qing F.-L., Gao W.-Z., Ying J. J. Org. Chem. 65:2000;2003-2006
49. (e) Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1. 2001;2491-2515.
50. (a) Neilsen A.T., Houlihan W. J. Org. React. 16:1968;1-438
51. (b) Mukaiyama T. Org. React. 28:1982;203-331
52. (c) Takazawa O., Kogami K., Hayashi K. Bull. Chem. Soc. Jpn. 58:1985;2427-2428
53. (d) Kawai M., Onaka M., Izumi Y. Bull. Chem. Soc. Jpn. 61:1988;1237-1245.
54. (a) Johnson J.R., Johns G. Org. React. 15:1967;204-599
55. (b) Bossio R., Marcaccini S., Pepino R., Torroba T. Synthesis. 1993;783-785.
56. 9.
57. Ciranni G., Clementi S. Tetrahedron Lett. 1971;3833-3836.
58. (a) Graziano M.L., Iesce M.R., Carli B., Scarpati R. Synthesis. 1983;125-126
59. (b) Haddadin M.J., Agha B.J., Tabri R.F. J. Org. Chem. 44:1979;494-497
60. (c) Ramirez F., Madan O.P., Smith C.P. J. Org. Chem. 30:1965;2284-2290
61. (d) Avery T.D., Taylor D.K., Tiekink R.T. J. Org. Chem. 65:2000;5531-5546.
62. Adembri G., De Sio F., Nesi R., Scotton M. J. Chem. Soc. (C). 1970;1536-1540.
63. (a) Smith M.B., March J. March's Advanced Organic Chemistry. 2001;Wiley, New York. pp 1062-1171
64. (b) Fringuelli F., Taticchi A. Dienes in the Diels-Alder Reaction. 1990;Wiley, New York. pp 177-261
65. (c) Fleming I. Pericyclic Reactions. 1999;Oxford University, Oxford.
66. (a) Alder K., Günzl W. Chem. Ber. 93:1960;809-825
67. (b) Stockmann H. J. Org. Chem. 26:1961;2025-2029
68. (c) Jones D.W., Wife R.L. J. Chem. Soc., Chem. Commun. 1973;421-422
69. (d) Smith J.R.S., Norman R.O.C., Stillings M.R. Tetrahedron. 34:1978;1381-1383.
70. (a) Lutz R.E., Rowlett R.J. Jr. J. Am. Chem. Soc. 70:1948;1359-1363
71. (b) Dien C.-K., Lutz R.E. J. Org. Chem. 21:1956;1492-1509
72. (c) Mosterd A., Matser H.J., Bos H.J.T. Tetrahedron Lett. 1974;4179-4180.
73. (a) Ramirez F., Madan O.P., Smith C.P. J. Org. Chem. 30:1965;2284-2290
74. (b) Haddadin M.J., Agha B.J., Tabri R.F. J. Org. Chem. 44:1979;494-497.
75. (a) Lutz R.E., Bauer C.R. J. Am. Chem. Soc. 73:1951;3456-3459
76. (b) Bailey P.S., Bath S.S., Thomsen W.F., Nelson H.H., Kawas E.E. J. Org. Chem. 21:1956;297-303.
77. Lutz R.E., Bauer C.R., Lutz R.G., Gillespie J.S. J. Org. Chem. 20:1955;218-224.
78. Lutz R.E., McGinn C.E. J. Am. Chem. Soc. 64:1942;2585-2588.
79. (a) Bailey P.S., Kawas E.E., Smith L.L. J. Am. Chem. Soc. 73:1951;4088-4090
80. (b) Bailey P.S., Pomerantz S.H. J. Am. Chem. Soc. 75:1953;281-284.
81. (a) Riley H.A., Gray A.R. Organic Synthesis. Collect. Vol. 2:1966;Wiley, New York. pp 509-511
82. (b) Mikol G.J., Russell G.A. Org. Synth. 5:1973;937-940.
83. Altomare A., Burla M.C., Camalli M., Cascarano M., Giacovazzo C., Guagliardi A., Polidori G. J. Appl. Crystallogr. 27:1994;435.
84. Crystal Structure Analysis Package; Molecular Structure Corporation, 1985 and 1992.