Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine

Tetrahedron

Volumn 65, Issue 24, 2009, Pages 4671-4680

  Ashoorzadeh, Amir ^a   Archibald, Glenn ^a   Caprio, Vittorio ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

3 BENZYLOXY 3,4,5,6 TETRAHYDROPYRIDINE N OXIDE; ALKENE DERIVATIVE; ANTIMALARIAL AGENT; FEBRIFUGINE; GLUTAMIC ACID; NITRONE; OXIDE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; RING OPENING; STEREOCHEMISTRY;

EID: 65149093079     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.044     Document Type: Article

References (93)

1. Koepfli J.B., Mead J.F., and Brockman Jr. J.A. J. Am. Chem. Soc. 69 (1947) 1837
2. Koepfli J.A., Mead J.F., and Brockman Jr. J.A. J. Am. Chem. Soc. 69 (1949) 1048-1054
3. Kopefli J.B., Brockman Jr. J.A., and Moffat J. J. Am. Chem. Soc. 72 (1950) 3323
4. Desideri N., Galli A., Sestili J., and Stein M.L. Arch. Pharm. 35 (1992) 490-501
5. Khuong-Huu Q., Ratle G., Monseur X., and Gouratel R. Bull. Soc. Chim. Belg. 81 (1972) 425-441
6. Guengerich F.P., DiMari S.J., and Broquist H.P. J. Am. Chem. Soc. 95 (1973) 2055-2056
7. Schneider M.J., Ungemach F.S., Broquist H.P., and Harris T.M. Tetrahedron 29 (1983) 29-32
8. El Nemr A. Tetrahedron 56 (2000) 8579-8629
9. For recent approaches to synthetic building blocks of this type see:
10. Jourdant J., and Zhu J. Tetrahedron Lett. 41 (2000) 7033-7036
11. Taniguchi T., and Ogasawara K. Org. Lett. 2 (2000) 3193-3195
12. Iradier F., Arrayás R.G., and Carretero J.C. Org. Lett. 2 (2001) 2957-2960
13. Okitsu O., Suzuki R., and Kobayashi S. J. Org. Chem. 66 (2001) 809-823
14. Fronicola R.S., Subbaraj K., and Montogomery J. Org. Lett. 4 (2002) 615-617
15. Monterde M.I., Brieva R., and Gotor V. Tetrahedron: Asymmetry 12 (2001) 525-528
16. Enders D., Nolte B., and Runsink J. Tetrahedron: Asymmetry 13 (2002) 587-593
17. Huang P.-Q., Liu L.-X., and Ruan Y.-P. Org. Lett. 5 (2003) 1927-1929
18. Katoh M., Matsune R., Nagase H., and Honda T. Tetrahedron Lett. 45 (2004) 6221-6223
19. Takahata H., Banba Y., Sasatani M., Nemoto H., Kato A., and Adachi I. Tetrahedron 60 (2004) 8199-8205
20. Bodas M., and Kumar P. Tetrahedron Lett. 45 (2004) 8461-8463
21. Wang Q., and Sasaki N.A. J. Org. Chem. 69 (2004) 4767-4773
22. Lemire A., Grenon M., Pourashraf M., and Charrette A.B. Org. Lett. 6 (2004) 3517-3520
23. Liang N., and Datta A. J. Org. Chem. 70 (2005) 10182-10185
24. Lemire A., and Charette A.B. Org. Lett. 7 (2005) 2747-2750
25. Liu L.-X., and Huang P.-Q. Tetrahedron: Asymmetry 17 (2006) 3265-3272
26. Kim I.S., Ji Y.J., and Jung Y.H. Tetrahedron Lett. 47 (2006) 7289-7293
27. Feng C.-G., Chen J., Ye J.-L., Ruan Y.-P., Zheng X., and Huang P.-Q. Tetrahedron 62 (2006) 7459-7465
28. For reviews see:
29. Merino P. Sci. Synth. 27 (2004) 511-580
30. Koumbis A.E., and Gallos J.E. Curr. Org. Chem. 7 (2003) 585-628
31. Lombardo M., and Trombini C. Curr. Org. Chem. 6 (2002) 695-713
32. Lombardo M., and Trombini C. Synthesis (2000) 759-774
33. De March P., Figueredo M., and Font J. Heterocycles 50 (1999) 1213-1226
34. Broggini G., and Zecchi G. Synthesis (1999) 905-917
35. Tsay S.-C., Patel H.V., and Hwu J.R. Synlett (1998) 939-949
36. Fredrickson M. Tetrahedron 53 (1997) 403-425
37. Confalone P.N., and Huie E.M. Org. React. 36 (1988) 1-127
38. Tufariello J.J. Acc. Chem. Res. 12 (1979) 396-403
39. Pulz R., Cicchi S., Brandi A., and Reißig H.-U. Eur. J. Org. Chem. (2003) 1153-1156
40. Cardona F., Goti A., and Brandi A. Org. Lett. 5 (2003) 1475-1478
41. Richichi B., Cicchi S., Chiacchio U., Romeo G., and Brandi A. Tetrahedron 59 (2003) 5231-5240
42. Pisaneschi F., Della Monica C., Cordero F.M., and Brandi A. Tetrahedron Lett. 43 (2002) 5711-5714
43. Cordero F.M., Pisaneschi F., Gensini M., Goti A., and Brandi A. Eur. J. Org. Chem. (2002) 1941-1951
44. Goti A., Cicchi S., Cacciarini M., Cardona F., Fedi V., and Brandi A. Eur. J. Org. Chem. (2000) 3633-3645
45. Zorn C., Anichini B., Goti B., Brandi A., Kozhushkov S.I., de Meijere A., and Citti L. J. Org. Chem. 64 (1999) 7846-7855
46. Goti A., Cacciarini M., Cardona F., and Brandi A. Tetrahedron Lett. 40 (1999) 2853-2856
47. Cardona F., Valenza S., Picasso S., Goti A., and Brandi A. J. Org. Chem. 63 (1998) 7311-7318
48. Murahashi S.-I., Ohtake H., and Imada Y. Tetrahedron Lett. 39 (1998) 2765-2766
49. Cicchi S., Goti A., and Brandi A. J. Org. Chem. 60 (1995) 4743-4748
50. Herczegh P., Kovacs I., Szilagyi L., Varga T., Dinya Z., and Sztaricskai F. Tetrahedron 34 (1993) 1211-1214
51. Van den Broek L.A.G.M. Tetrahedron 52 (1996) 4467-4487
52. Peer A., and Vasella A. Helv. Chim. Acta 82 (1999) 1044-1065
53. Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., and Pope A.J. Bioorg. Med. Chem. Lett. 10 (2000) 1811-1814
54. Duff F.J., Vivien V., and Wightman R.H. Chem. Commun. (2000) 2127-2128
55. Brandi A., Cicchi S., Paschetta V., Pardo D.G., and Cossy J. Tetrahedron Lett. 43 (2002) 9357-9359
56. Tamura O., Toyao A., and Ishibashi H. Synlett (2002) 1344-1346
57. Ooi H., Urushibara A., Esumi T., Iwabuchi Y., and Hatakeyama S. Org. Lett. 3 (2001) 953-955
58. Ashoorzadeh A., and Caprio V. Synlett (2005) 346-348
59. Keck G.E., Andrus M.B., and Romer D.R. J. Org. Chem. 56 (1991) 417-420
60. Masaguer C.F., Bleriot Y., Charlwood J., Winchester B.G., and Fleet G.W.J. Tetrahedron 53 (1997) 15147-15156
61. Gmiener P., and Dagmar J. J. Org. Chem. 60 (1995) 3910-3915
62. For recent examples see:
63. AliSk A. Tetrahedron Lett. 34 (1993) 5325-5326
64. Macours P., Braekman J.C., and Daloze D. Tetrahedron 51 (1995) 1415-1428
65. Cordero F.M., Machetti F., De Sarlo F., and Brandi A. Gazz. Chim. Ital. 127 (1997) 25-29
66. Tian L., Xu G.-Y., Ye Y., and Liu L.-Y. Synlett (2003) 1329-1334
67. Cicchi S., Maradi M., Goti A., and Brandi. Tetrahedron Lett. 42 (2001) 6503-6505
68. Ali Sk.A., and Wazeer I.M. J. Chem. Soc., Perkin Trans. 1 (1988) 597-605
69. Goti A., Cicchi S., Fedi V., Nannelli L., and Brandi A. J. Org. Chem. 62 (1997) 3119-3125
70. Camiletti C., Dhavale D.D., Gentilucci L., and Trombini C. J. Chem. Soc., Perkin Trans. 1 (1993) 3157-3165
71. Cicchi S., Bonanni M., Cardona F., Revuelta J., and Goti A. Org. Lett. 5 (2003) 1773-1776
72. Na H.S., Yu J., Shin J.J., Yoo K.H., Kim D.J., and Park S.W. Heterocycles 48 (1998) 2365-2378
73. Jang C.S., Fu F.Y., Wang C.Y., Huang K.C., Lu G., and Thou T.C. Science 103 (1946) 59
74. Hewitt R.I., Wallace W.S., Gill E.R., and Williams J.H. Am. J. Trop. Med. Hyg. 1 (1952) 768-772
75. Murata K., Takano F., Fushiya S., and Oshima Y. Biochem. Pharmacol. 58 (1999) 1593-1601
76. For other syntheses of febrifugine see:. Baker B.R., Schaub R.E., McEvoy F.J., and Williams J.H. J. Org. Chem. 17 (1952) 132-140
77. Baker B.R., Schaub R.E., McEvoy F.J., and Williams J.H. J. Org. Chem. 18 (1953) 153-177
78. Baker B.R., McEvoy F.J., Schaub R.E., Joseph J.P., and Williams J.H. J. Org. Chem. 18 (1953) 178-183
79. Baker B.R., and McEvoy F.J. J. Org. Chem. 20 (1955) 118-135
80. Baker B.R., and McEvoy F.J. J. Org. Chem. 20 (1955) 136-142
81. Hill R.K., and Edwards A.G. Chem. Ind. (London) (1962) 858
82. Barringer Jr. D.F., Beakelhammer G.B., and Wayne R.S. J. Org. Chem. 38 (1973) 1937-1940
83. Burgess L.E., Gross E.K.M., and Jurka J. Tetrahedron Lett. 37 (1996) 3225-3258
84. Takeuchi Y., Hattori M., Abe H., and Harayama T. Synthesis (1999) 1814-1818
85. Kobayashi S., Ueno M., Suzuki R., Ishitani H., Kim H.-S., and Wataya S. J. Org. Chem. 64 (1999) 6833-6841
86. Takeuchi Y., Azuma K., Takakura K., Abe H., and Harayama T. Chem. Commun. (2000) 1643-1644
87. Okitsu O., Suzuki R., and Kobayashi S. Synlett (2000) 989-990
88. Takeuchi Y., Azuma K., Takakura K., Abe H., Kim H.-S., Wataya Y., and Harayama T. Tetrahedron 57 (2001) 1213-1218
89. Sugiura M., Hagio H., Hirabayashi R., and Kobayshi S. J. Am. Chem. Soc. 123 (2001) 12510-12517
90. Takeuchi Y., and Harayama T. Trends Heterocycl. Chem. 7 (2001) 65-74
91. Takeuchi Y., Oshige M., Azuma K., Abe H., and Harayama T. Chem. Pharm. Bull. 53 (2005) 868-869
92. Katoh M., Matsune R., and Honda T. Heterocycles 67 (2006) 189-204
93. Ranganathan D., Rathi R., Kesavan K., and Pal Singh W. Tetrahedron 42 (1986) 4873-4878