An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

Tetrahedron Letters

Volumn 48, Issue 11, 2007, Pages 1907-1910

  Bisai, Alakesh ^a   Singh, Vinod K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKALOID DERIVATIVE; ALLOSEDAMINE; ASPARTIC ACID DERIVATIVE; CONIINE; HALOSILANE; PIPERIDINE; PIPERIDINE DERIVATIVE; SEDAMINE; SEDRIDINE; SILANE DERIVATIVE; TETRAPONERINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; MITSUNOBU REACTION; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 33846897164     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.082     Document Type: Article

References (52)

1. Strunzand G.M., and Finlay J.A. In: Brossi A. (Ed). The Alkaloids Vol. 26 (1985), Academic Press, New York 89-174
2. For a review on the synthesis of piperdines, see:. Buffat M.G.P. Tetrahedron 60 (2004) 1701
3. For details about coniine, see a recent review on Hemlock alkaloids:. Reynolds T. Phytochemistry 66 (2005) 1399 and references cited therein
4. For the most recent paper on asymmetric syntheses of coniine and related alkaloids, see:. Wu T.R., and Chong J.M. J. Am. Chem. Soc. 128 (2006) 9646
5. Marion L. Can. J. Res. 23B (1945) 165
6. Marion L., Lavigne R., and Lemay L. Can. J. Chem. 29 (1951) 347
7. Franck B. Chem. Ber. 91 (1958) 2803
8. Franck B. Chem. Ber. 93 (1960) 2360
9. Fodor G., Butruille D., Huber S.C., and Letourneau F. Tetrahedron 27 (1971) 2055 and references cited therein
10. Kim J.H., Hart H.T., and Stevens J.F. Phytochemistry 41 (1996) 1319
11. Weiland H., Koschara K., Dane E., Renz J., Schwarze W., and Linde W. Liebigs Ann. Chem. 540 (1939) 103
12. Schopf C., Kauffmann T., Berth P., Bundschuh W., Dummer G., Fett H., Habermehl G., Wieters E., and Wust W. Liebigs Ann. Chem. 608 (1957) 88
13. Gershwin M.E., and Terr A. Clin. Rev. Allergy Immunol. 14 (1996) 241
14. For a review on syntheses of sedum and related alkaloids, see:. Bates R.W., and Sa-Ei K. Tetrahedron 58 (2002) 5957
15. For a general account on the asymmetric synthesis of substituted piperidines, see:. Bailey P.D., Millwood P.A., and Smith P.D. Chem. Commun. (1998) 633
16. For selected syntheses of chiral sedamine, see:. Yadav J.S., Reddy M.S., Rao P.P., and Prasad A.R. Tetrahedron Lett. 47 (2006) 4397
17. Bates R.W., and Boonsombat J. Org. Biomol. Chem. 3 (2005) 520
18. Josephsohn N.S., Snapper M.L., and Hoveyda A.H. J. Am. Chem. Soc. 126 (2004) 3734
19. Angoli M., Barilli A., Lesma G., Passarella D., Riva S., Silvani A., and Danieli B. J. Org. Chem. 68 (2003) 9525
20. Cossy J., Willis C., Bellosta V., and Bouzbouz S. J. Org. Chem. 67 (2002) 1982 and references cited therein
21. For syntheses of (-)-allosedamine, see:. Raghavan S., and Rajender A. Tetrahedron Lett. 60 (2004) 5059
22. Felpin F.-X., and Lebreton J. Tetrahedron Lett. 43 (2002) 225
23. Oppolzer W., and Deerberg J.O. Helv. Chim. Acta 77 (1994) 554
24. For a synthesis of (+)-allosedamine, see:. Kang B., and Chang S. Tetrahedron 60 (2004) 7353
25. For asymmetric syntheses of sedridine and allosedridine, see:. Davis F.A., Prasad K.R., Nolt M.B., and Wu Y. Org. Lett. 5 (2003) 925
26. Takahata H., Kubota M., and Ikota N. J. Org. Chem. 64 (1999) 8594
27. Louis C., and Hottele C. Tetrahedron: Asymmetry 8 (1997) 109
28. Littler B.J., Gallagher T., Boddy I.K., and Riordan P.D. Synlett (1997) 22
29. Micel K.-H., Sandberg F., Haglid F., and Norin T. Acta Pharm. Suec. 4 (1967) 97
30. Micel K.-H., Sandberg F., Haglid F., Norin T., Chan R.P.K., and Craig J.C. Acta Chem. Scand. 23 (1969) 3479
31. For asymmetric syntheses of halosaline, see:. Lesma G., Crippa S., Danieli B., Passarella D., Sacchetti A., Silvani A., and Virdis A. Tetrahedron 60 (2004) 6437
32. Kochi T., Tang T.P., and Ellman J.A. J. Am. Chem. Soc. 125 (2003) 11276
33. Stragies R., and Blechart S. Tetrahedron 55 (1999) 8179
34. Merlin P., Braekman J.C., Daloze D., and Pasteels J.M. J. Chem. Ecol. 14 (1988) 517
35. Braekman J.C., Daloze D., Pasteels J.M., Vanhecke P., Declercq J.P., Sinnwell V., and Franke W.Z. Naturforsch. 42c (1987) 627
36. Charette A.B., Matheiu S., and Martel J. Org. Lett. 7 (2005) 5401 and references cited therein
37. Kim J.T., Butt J., and Gevorgyan V. J. Org. Chem. 69 (2004) 5638
38. Kim J.T., and Gevorgyan V. Org. Lett. 4 (2002) 4697
39. Takahata H., Kubota M., and Ikota N. J. Org. Chem. 64 (1999) 8594
40. Barluenga J., Tomas M., Kouznetsov V., and Rubio E. J. Org. Chem. 59 (1994) 3699
41. Merlin P., Braekman J.C., and Daloze D. Tetrahedron 47 (1991) 3805
42. Stragies R., and Blechert S. J. Am. Chem. Soc. 122 (2000) 9584
43. Yue C., Gauthier I., Royer J., and Husson H.-P. J. Org. Chem. 61 (1996) 4949 and references cited therein
44. Devijver C., Macours P., Braekman J.C., Daloze D., and Pasteels J.M. Tetrahedron 51 (1995) 10913
45. Yue C.Y., Royer J., and Husson H.-P. J. Org. Chem. 55 (1990) 1140
46. Yuxin P., Katja B., Emilie B., Lars H., Fredrik L., and Christina M. Eur. J. Org. Chem. 13 (2005) 2835
47. Argouarch G., Stones G., Gibson C.L., Kennedy A.R., and Sherrington D.C. Org. Biomol. Chem. 1 (2003) 4408 and references cited therein
48. Prasad B.A.B., Bisai A., and Singh V.K. Org. Lett. 6 (2004) 4829
49. Pandey M.K., Bisai A., Pandey A., and Singh V.K. Tetrahedron Lett. 46 (2005) 5039
50. For the synthesis of (S)-N-tosyl-coniine, see:. Eskici M., and Gallagher T. Synlett (2000) 1360
51. For (R)-N-tosyl-coniine, see:. Kim Y.H., and Choi J.Y. Tetrahedron Lett. 37 (1996) 5543
52. Takahata H., Kubota M., and Momose T. Tetrahedron Lett. 38 (1997) 3451