An enantioselective synthesis of (+)-azimic acid

Tetrahedron Asymmetry

Volumn 20, Issue 10, 2009, Pages 1181-1184

  Xiao, Kai Jiong ^a   Liu, Liang Xian ^a   Huang, Pei Qiang ^a,b  

^a Key Laboratory for Chemical Biology of Fujian Province   (China)

^b State Key Laboratory of Bioorganic and Natural Products Chemistry   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; AZIMIC ACID; IMIDE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 66149182881     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.04.008     Document Type: Article

References (83)

1. For reviews on the piperidine alkaloids, see: Angle, S. R.; Breitenbucher, J. G. Recent Progress in the Synthesis of Piperidine and Indolizidine Alkaloids. In Studies in Natural Products Chemistry, 1995; Vol. 16, Part 10, pp 453-502.
2. Schneider M. Pyridine and Piperidine Alkaloids: An Update. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biochemical Perspectives Vol. 10 (1996), Elsevier Science, Oxford 155-299
3. Ojima, I.; Iula, D. M.; New Approaches to the Syntheses of Piperidine, Pyrrolizidine, and Quinazoline Alkaloids by Means of Transition Metal Catalyzed Carbonylations. In Alkaloids: Chemical and Biological Perspectives, 1999; Vol. 13, pp 371-412.
4. Michael J.P. Nat. Prod. Rep. 25 (2008) 139-165
5. O'Hagan D. Nat. Prod. Rep. 17 (2000) 435-446
6. Sansores-Peraza P., Rosado-Vallado M., Brito-Loeza W., Mena-Rejón G.J., and Quijano L. Fitoterapia 71 (2000) 690-692
7. Viegas Jr. C., Bolzani V.S., Pimentel L.S.B., Castro N.G., Cabral R.F., Costa R.S., Floyd C., Rocha M.S., Young M.C.M., Barreiro E.J., and Fraga C.A.M. Bioorg. Med. Chem. 13 (2005) 4184-4190
8. Viegas Jr. C., Silva D.H.S., Pivatto M., de Rezende A., Castro-Gambôa I., Bolzani V.S., and Nair M.G. J. Nat. Prod. 70 (2007) 2026-2028
9. Viegas Jr. C., Alexandre-Moreira M.S., Fraga C.A.M., Barreiro E.J., da Silva Bolzani V., and de Miranda A.L.P. Chem. Pharm. Bull. 56 (2008) 407-412
10. Castro N.G., Costa R.S., Pimentel L.S.B., Danuello A., Romeiro N.C., Viegas Jr. C., Barreiro E.J., Fraga C.A.M., Bolzani V.S., and Rocha M.S. Eur. J. Pharmacol. 580 (2008) 339-349
11. Isolation and structure determination:. Rall G.J.H., Smalberger T.M., and de Waal H.L. Tetrahedron Lett. 8 (1967) 3465-3469
12. Smalberger T.M., Rall G.J.H., de Waal H.L., and Arndt R.R. Tetrahedron 24 (1968) 6417-6421
13. Isolation and structure determination:. Rapoport H., and Baldridge Jr. H.D. J. Am. Chem. Soc. 73 (1951) 343-346
14. Govindachari T.R., Pai B.R., and Narasimhan N.S. J. Chem. Soc. (1954) 1847-1849
15. Govindachari T.R., and Narasimhan N.S. J. Chem. Soc. (1955) 1563-1565
16. Spiteller-Friedmann M., and Spiteller G. Monatsh. Chem. 95 (1964) 1234-1241
17. Govindachari T.R., Nagarajan K., and Viswanathan N. Tetrahedron Lett. 6 (1965) 1907-1916
18. Coke J.L., and Rice Jr. W.Y. J. Org. Chem. 30 (1965) 3420-3422
19. Strünz G.M., and Findlay J.A. In: Brossi A. (Ed). The Alkaloids Vol. 26 (1985), Academic Press, New York 89-182
20. Sato T., Aoyagi S., and Kibayashi C. Org. Lett. 5 (2003) 3839-3842
21. Corey E.J., and Nicolaou K.C. J. Am. Chem. Soc. 96 (1974) 5614-5616
22. Corey E.J., Nicolaou K.C., Lawrence S., and Melvin Jr. S. J. Am. Chem. Soc. 97 (1975) 654-655
23. For the synthesis of racemic azimic acid, see:. Brown E., and Dhal R. Tetrhaedron Lett. 15 (1974) 1029-1032
24. Brown E., and Dhal R. J. Chem. Soc., Perkin Trans. 1 (1976) 2190-2193
25. Natsume M., and Ogawa M. Heterocycles 14 (1980) 169-173
26. Hasseberg H.-A., and Gerlach H. Liebigs Ann. Chem. (1989) 255-261
27. Leverett C.A., Cassidy M.P., and Padwa A. J. Org. Chem. 71 (2006) 8591-8601
28. For the synthesis of (+)-azimic acid, see:. Hanessian S., and Frenette R. Tetrahedron Lett. 20 (1979) 3391-3394
29. Lu Z.-H., and Zhou W.-S. Tetrahedron 49 (1993) 4659-4664
30. Kiguchi T., Shirakawa M., Ninomiya I., and Naito T. Chem. Pharm. Bull. 44 (1996) 1282-1284
31. Kiguchi T., Shirakawa M., Honda R., Ninomiya I., and Naito T. Tetrahedron 54 (1998) 15589-15606
32. Kumar K.K., and Datta A. Tetrahedron 55 (1999) 13899-13906
33. Ma D., and Ma N. Tetrahedron Lett. 44 (2003) 3963-3965
34. Ref. 6.
35. For the synthesis of racemic carpamic acid, see:. Brown E., and Bourgouin A. Chem. Lett. (1974) 109-112
36. Brown E., and Bourgouin A. Tetrahedron 31 (1975) 1047-1051
37. Holmes A.B., Swithenbank C., and Williams S.F. J. Chem. Soc., Chem. Commun. (1986) 265-266
38. For the synthesis of (+)-carpamic acid, see:. Singh R., and Ghosh S.K. Tetrahedron Lett. 43 (2002) 7711-7715
39. Randl S., and Blechert S. Tetrahedron Lett. 45 (2004) 1167-1169
40. For the synthesis of spectaline and/or cassine, see:. Makabe H., Kong L.K., and Hirota M. Org. Lett. 5 (2003) 27-29
41. Lee Y.-S., Shin Y.-H., Kim Y.-H., Lee K.-Y., Oh C.-Y., Pyun S.-J., Park H.-J., Jeong J.-H., and Ham W.-H. Tetrahedron: Asymmetry 14 (2003) 87-93
42. Toyooka N., Yoshida Y., Yotsui Y., and Momose T. J. Org. Chem. 64 (1999) 4914-4919
43. Momose T., Toyooka N., and Jin M. J. Chem. Soc., Perkin Trans. 1 (1997) 2005-2013
44. Oetting J., Holzkamp J., Meyer H.H., and Pahl A. Tetrahedron: Asymmetry 8 (1997) 477-484
45. Toyooka N., Yoshida Y., and Momose T. Tetrahedron Lett. 36 (1995) 3715-3718
46. Momose T., and Toyooka N. Tetrahedron Lett. 34 (1993) 5785-5788
47. For the syntheses of deoxocassine, see:. Kurihara K., Sujimoto T., Saitoh Y., Igarashi Y., Hirota H., Moriyama Y., Tsuyuki T., Takahashi T., and Khuong-Huu Q. Bull. Chem. Soc. Jpn. 58 (1985) 3337 other alkaloids and analogues
48. Nakatani Y., Oshita J., Ishigami K., Watanabe H., and Kitahara T. Tetrahedron 62 (2006) 160-165
49. Ma N., and Ma D.-W. Chin. J. Org. Chem. 21 (2003) 1356-1359
50. Koulocheri S.D., Pitsinos E.N., and Haroutounian S.A. Synthesis (2002) 111-115
51. Enders D., and Kirchhoff J.H. Synthesis (2000) 2099-2105
52. Pahl A., Wartchow R., and Meyer H.H. Tetrahedron Lett. 39 (1998) 2095-2096
53. Pahl A., Oetting J., Holzkamp J., and Meyer H.H. Tetrahedron 53 (1997) 7255-7266
54. Huang P.-Q., Liu L.-X., Wei B.-G., and Ruan Y.-P. Org. Lett. 5 (2003) 1927-1930
55. Huang P.-Q., Wei B.-G., and Ruan Y.-P. Synlett (2003) 1663-1667
56. Liu L.-X., Ruan Y.-P., Guo Z.-Q., and Huang P.-Q. J. Org. Chem. 69 (2004) 6001-6009
57. Yu D.-S., Xu W.-X., Liu L.-X., and Huang P.-Q. Synlett (2008) 1189-1192
58. Huang P.-Q., Guo Z.-Q., and Ruan Y.-P. Org. Lett 8 (2006) 1435-1438
59. For some other approaches to chiral non-racemic 6-substituted 5-hydroxy-2-piperidinones, see:. Lee H.K., Chun J.S., and Pak C.S. Tetrahedron 59 (2003) 6445-6454
60. Koulocheri S.D., Magiatis P., Skaltsounis A.L., and Haroutounian S.A. Tetrahedron 58 (2002) 6665-6671
61. Barros M.T., Januario-Charmier M.A., Maycock C.D., and Michaud T. Tetrahedron 58 (2002) 1519-1524
62. Bach T., Bergmann H., Brummerhop H., Lewis W., and Harms K. Chem. Eur. J. 7 (2001) 4512-4521
63. Ha J.D., and Cha J.K. J. Am. Chem. Soc. 121 (1999) 10012-10020
64. Folmer J.J., Acero C., Thai D.L., and Rapoport H. J. Org. Chem. 63 (1998) 8170-8182
65. Oishi T., Iwakuma T., Hirama M., and Ito S. Synlett (1995) 404-406
66. Hembre E.J., and Pearson W.H. Tetrahedron 53 (1997) 11021-11032
67. For some typical strategies, see:. Zhang Y.Q., and Liebeskind L.S. J. Am. Chem. Soc. 128 (2006) 465-472
68. Comins D.L., Kuethe J.T., Miller T.M., Fevrier F.C., and Brooks C.A. J. Org. Chem. 70 (2005) 5221-5234
69. Comins D.L., Joseph S.P., Hong H., Al-awar R.S., Foti C.J., +Zhang Y.-M., Chen X., LaMunyon D.H., and Guerra-Weltzien M. Pure Appl. Chem. 69 (1997) 477-481
70. Viana G.H.R., Santos I.C., Alves R.B., Gil L., Marazano C., and de Freitas Gil R.P. Tetrahedron Lett. 46 (2005) 7773-7776
71. Escolano C., Amat M., and Bosch J. Chem. Eur. J. 12 (2006) 8198-8207
72. Husson H.-P., and Royer J. Chem. Soc. Rev. 28 (1999) 383-394
73. Liu L.-X., Xiao K.-J., and Huang P.-Q. Tetrahedron 65 (2009) 3834-3841
74. Giovannini A., Savoia D., and Umani-Ronchi A. J. Org. Chem. 54 (1989) 228-233
75. For some applications, see:. Yoda H., Nakajima T., and Takabe K. Tetrahedron Lett. 37 (1996) 5531-5534
76. Kanazawa A., Gillet S., Derlair P., and Greene A.E. J. Org. Chem. 63 (1998) 4660-4663
77. Huang P.-Q., Wu T.-J., and Ruan Y.-P. Org. Lett. 5 (2003) 4341-4344
78. For recent improvements, see:. Brennema J.B., and Martin S.F. Org. Lett 6 (2004) 1329-1331
79. Rudolph A.C., Machauer R., and Martin S.F. Tetrahedron Lett. 45 (2004) 4895-4898
80. Brenneman J.B., Machauer R., and Martin S.F. Tetrahedron 60 (2007) 7301-7314
81. Kelly D.R., Roberts S.M., and Newton R.F. Synth. Commun. 9 (1979) 295-299
82. Carlson P.H.J., Kabuki T., Martin V.S., and Sharpless K.B. J. Org. Chem. 46 (1981) 3936-3938
83. Nunez M.T., and Martin V.S. J. Org. Chem. 55 (1990) 1928-1932