A concise and diastereoselective synthesis of piperidine and indolizidine alkaloids via aza-Prins cyclization

Synthesis

Volumn 2012, Issue 2, 2012, Pages 297-303

  Reddy, Basi V Subba ^a   Chaya, Dudhmal N ^a   Yadav, Jhillu S ^a   Grée, René ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

alkaloids; aza Prins cyclization; diastereoselective; natural products; piperidine

Indexed keywords

ALKALOIDS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE SYNTHESIS; NATURAL PRODUCTS; PIPECOLIC ACID; PIPERIDINE;

METABOLITES; NITROGEN COMPOUNDS; PIPE; STEREOSELECTIVITY;

CYCLIZATION;

4 HYDROXY 2 HYDROXYMETHYLPIPERIDINE; 4 HYDROXYPIPECOLIC ACID; CONICEINE; CONIINE; INDOLIZIDINE ALKALOID; PIPECOLIC ACID; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AZA PRINS CYCLIZATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84855646368     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289648     Document Type: Article

References (76)

1. Jones T H., Blum M S., In Alkaloids: Chemical and Biological Perspectives Vol. 1 Pelletier S W. Wiley New York 1983 Chap. 2 33
2. Fodor G B., Colasanti B, In Alkaloids: Chemical and Biological Perspectives Vol. 3 Pelletier S W. Wiley New York 1985 Chap. 1 1-90
3. Schneider M J., In Alkaloids: Chemical and Biological Perspectives Vol. 10 Pelletier S W. Wiley New York 1986 Chap. 3 155
4. Trunz G M., Findlay J A., In The Alkaloids Brossi A Academic London 1985 Chap. 3 89
5. Numata A, Ibuka I, In The Alkaloids Vol. 31 Brossi A Academic New York 1987 193
6. Angle R S., Breitenbucher J G., Studies in Natural Products Chemistry, In Stereoselective Synthesis (Part J) Vol. 16 Atta-ur-Rahman Elsevier Amsterdam 1995 453
7. Gershwin M E., Terr A, Clin. Rev. Allergy Immunol. 1996 14 241
8. Micel K H., Sandberg F, Haglid F, Norin T, Acta Pharm. Suec. 1967 4 97
9. Micel K H., Sandberg F, Haglid F, Norin T, Chan R P. K., Craig J C., Acta Chem. Scand. 1969 23 3479
10. Kallstrom S, Leino R, Bioorg. Med. Chem. 2008 16 601
11. Wenzel B, Sorger D, Heinitz K, Scheunemann M, Schliebs R, Steinbach J, Sabri O, Eur. J. Med. Chem. 2005 40 1197
12. Guzikowski A P., Tamiz A P., Acosta-Burruel M, Hong-Bae S, Cai S X., Hawkinson J E., Keana J F., Kesten S R., Shipp C T., Tran M, Whittermore E R., Woodward R M., Wright J L., Zhou Z L., J. Med. Chem. 2000 43 984; and references cited therein
13. Watson A A., Fleet G W. J., Asano N, Molyneux R J., Nash R J., Phytochemistry 2001 56 265
14. Daly J W., Spande T F., Garraffo H M., J. Nat. Prod. 2005 68 1556
15. Asano N, Curr. Top. Med. Chem. 2003 3 471
16. Howard N, Abell C, Blakemore W, Chessari G, Congreve M, Howard S, Jhoti H, Murray C W., Seavers L C. A., VanMontfort R L. M., J. Med. Chem. 2006 49 1346
17. Zhou Y, Gregor V E., Ayida B K., Winters G C., Sun Z, Murphy D, Haley G, Bailey D, Froelich J M., Fish S, Webber S E., Hermann T, Wall D, Bioorg. Med. Chem. Lett. 2007 17 1206
18. Baliah V, Jeyaraman R, Chandrasekaran L, Chem. Rev. 1983 83 379
19. Horton D A., Bourne G T., Smythe M L., Chem. Rev. 2003 103 893
20. Michael J P., Nat. Prod. Rep. 2008 25 139
21. Peters R, Jautze S, Synthesis 2010 365
22. Hiemstra H, Marcelli T, Synthesis 2010 1229
23. Huang Y, Domling A, Synthesis 2010 2859
24. Felpin F X., Lebreton J, Eur. J. Org. Chem. 2003 3693
25. Couty F, Amino Acids 1999 16 297
26. Buffat M G. P., Tetrahedron 2004 60 1701; and references therein
27. Speckamp W N., Hiemstra H, Tetrahedron 1985 41 4367
28. Shipman M, Clarkson G J., Wynne E, Tetrahedron Lett. 2008 49 250
29. Bailey P D., Millwood P A., Smith P D., Chem. Commun. 1998 633
30. Cortez G A., Schrock R R., Hoveyda A H., Angew. Chem. Int. Ed. 2007 46 4534
31. Watson P S., Jiang B, Scott B, Org. Lett. 2000 2 3679
32. Carballo R M., Ramirez M A., Rodriguez M L., Martin V S., Padron J I., Org. Lett. 2006 8 3837
33. Kishi Y, Nagura H, Inagi S, Fuchigami T, Chem. Commun. 2008 3876
34. Yadav J S., Reddy B V. S., Chaya D N., Kumar G G. K. S. N., Naresh P, Aravind S, Kunwar A C., Madavi C, Tetrahedron Lett. 2008 49 3330
35. Yadav J S., Reddy B V. S., Chaya D N., Kumar G G. K. S. N., Naresh P, Jagadeesh B, Tetrahedron Lett. 2009 50 1799
36. Guerrier L, Royer J, Grierson D S., Husson H, J. Am. Chem. Soc. 1983 105 7754
37. Moody C J., Lightfoot A P., Gallagher P T., J. Org. Chem. 1997 62 746
38. Klegraf E, Follmann M, Schollmeyer D, Kunz H, Eur. J. Org. Chem. 2004 3346
39. Airiau E, Girard N, Pizzeti M, Salvadori J, Taddei M, Mann A, J. Org. Chem. 2010 75 8670
40. Chattopadhyay S K., Biswas T, Biswas T, Tetrahedron Lett. 2008 49 1365
41. Vink M K. S., Schortinghuis C A., Luten J, vanMaarseveen J H., Schoemaker H E., Hiemstra H, Rutjes F P. J. T., J. Org. Chem. 2002 67 7869
42. Rutjes F P. J. T., Veerman J J. N., Meester W J. N., Hiemstra H, Schoemaker H E., Eur. J. Org. Chem. 1999 1127
43. Lemire A, Charette A B., J. Org. Chem. 2010 75 2077
44. Fadel A, Lahrache N, J. Org. Chem. 2007 72 1780
45. Sibi M P., Christensen J W., J. Org. Chem. 1999 64 6434
46. Wilson S R., Sawicki R A., J. Org. Chem. 1979 44 330
47. Hart D J., Tsai Y.-M, Choi J.-K, Burnett D A., J. Am. Chem. Soc. 1984 106 8201
48. For the data of compound E, see:, Takahata H, Banba Y, Ouchi H, Nemoto H, Kato A, Adachi I, J. Org. Chem. 2003 68 3603
49. Lebrun S, Couture A, Deniau E, Grandclaudon P, Tetrahedron: Asymmetry 2008 19 1245
50. Vetter J, Food Chem. Toxicol. 2004 42 1373
51. Reynolds T R., Phytochemistry 2005 66 1399
52. Davis F A., Song M, Augustine A, J. Org. Chem. 2006 71 2779
53. Lu Z.-H, Zhou W.-S, Tetrahedron 1993 49 4659
54. Lamarre D, Croteau G, Bourgon L, Thibeault D, Wardrop E, Clouette C, Vaillancourt M, Cohen E, Pargellis C, Yoakim C, Anderson P, Antimicrob. Agents Chemother. 1997 41 965
55. Wu W J., Raleigh D P., J. Org. Chem. 1998 63 6689
56. Cowell S M., Lee Y S., Cain J P., Hurby V J., Curr. Med. Chem. 2004 11 2785
57. Komoto T, Yano K, Ono J, Okawa J, Nakajima T, JP Patent 61035788 1986, Takemoto Y, Ueda S, Takeuchi J, Nakmoto T, Iwata C, Tetrahedron Lett. 1994 35 8821
58. Beaulieu P L., Lavallee P, Abraham A, Anderson P C., Boucher C, Bousquet Y, Duceppe J, Gillard J, Gorys V, Grand-Maitre C, Grenier L, Guindon Y, Guse I, Plamondon L, Soucy F, Valois S, Wernic D, Yoakim C, J. Org. Chem. 1997 62 3440, Anderson P C., Souey F, Yoakim C, Lavallee P, Beaulieu P L., US Patent 5.545.640 1996
59. Liang N, Datta A, J. Org. Chem. 2005 70 10182
60. Nair L G., Saksena A, Lovey R, Sannigrahi M, Wong J, Kong J, Fu X, Girijavallabhan V, J. Org. Chem. 2010 75 1285
61. Confalonieri G, Marrotta E, Rama F, Righi P, Rosini G, Serra R, Venturelli F, Tetrahedron 1994 50 3235
62. Morrison R I., Biochem. J. 1953 53 474
63. Pastuszak I, Molyneux R J., James L F., Elbein A D., Biochemistry 1990 29 1886
64. Portoghese P S., Pazdernik T L., Kuhn W L., Hite G, Shafiee A, J. Med. Chem. 1968 11 12
65. Tanaka H, Kuroda A, Marusawa H, Hatanaka H, Kino T, Goto T, Hashimoto M, Taga T, J. Am. Chem. Soc. 1987 109 5031
66. Ireland R E., Gleason J L., Gegnas L D., Highsmith T K., J. Org. Chem. 1996 61 6856
67. Swindells D C. N., White P S., Findlay J A., Can. J. Chem. 1978 56 2491
68. Smith A B. III, Condon S M., McCauley J A., Leazer J L. Jr, Leahy J W., Maleczka R E. Jr, J. Am. Chem. Soc. 1997 119 962
69. Pastuszak I, Molyneux R J., James L F., Elbein A D., Biochemistry 1990 29 1886
70. Skiles J W., Giannousis P P., Fales K R., Bioorg. Med. Chem. Lett. 1996 6 963
71. Michael J P., Nat. Prod. Rep. 2005 22 603
72. Erspamer V, Melchiorri P, Trends Pharmacol. Sci. 1980 1 391
73. Aronstam R S., Daly J W., Spande T F., Narayanan T K., Albuquerque E X., Neurochem. Res. 1986 11 1227
74. Xiaotao P, Dawei M, J. Org. Chem. 2003 68 4400
75. Padwa A, Harris J M., J. Org. Chem. 2003 68 4371
76. Baskaran S, Kumar G D. K., J. Org. Chem. 2005 70 4520