A facile synthetic route to (+)-allosedamine via hydrolytic kinetic resolution and olefin metathesis

Tetrahedron

Volumn 60, Issue 34, 2004, Pages 7353-7359

  Kang, Byungman ^a   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

Allosedamine; Hydrolytic kinetic resolution; Ring closing metathesis; Total synthesis

Indexed keywords

ALKENE DERIVATIVE; AMINE; COBALT; HERBACEOUS AGENT; LOBELIA INFLATA EXTRACT; PLANT EXTRACT; RUTHENIUM; UNCLASSIFIED DRUG;

CATALYSIS; CONFERENCE PAPER; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROLYSIS KINETICS; LOBELIA; PRIORITY JOURNAL; RING CLOSING METATHESIS;

EID: 3342913784     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.054     Document Type: Conference Paper

References (58)

1. Dwoskin L.P., Crooks P.A. Biochem. Pharmacol. 63:2002;89-98
2. Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;41-63 Wiley, New York
3. Shono T., Matsumura Y., Tsubata K. J. Am. Chem. Soc. 103:1981;1172-1176
4. Tirel P.-J., Vaultier M., Carrié R. Tetrahedron Lett. 30:1989;1947-1950
5. Pilli R.A., Dias L.C. Synth. Commun. 21:1991;2213
6. Ozawa N., Nakajima S., Zaoya K., Hamaguchi F., Nagasaka T. Heterocycles. 32:1991;889-894
7. Comins D.L., Hong H. J. Org. Chem. 58:1993;5035-5036
8. Yu C.-Y., Meth-Cohn O. Tetrahedron Lett. 40:1999;6665-6668
9. Cossy J., Willis C., Bellosta V., BouzBouz S. J. Org. Chem. 67:2002;1982-1992
10. Felpin F.-X., Lebreton J. J. Org. Chem. 67:2002;9192-9199
11. Wakabayashi T., Watanabe K., Kato Y., Saito M. Chem. Lett. 1977;223-228
12. Liguori A., Ottana R., Romeo G., Sindona G., Uccellla N. Chem. Ber. 122:1989;2019-2020
13. Oppolzer W., Deerberg J., Tamura O. Helv. Chim. Acta. 77:1994;554-560
14. Meth-Cohn O., Yau C.C., Yu C.-Y. J. Heterocyclic Chem. 36:1999;1549-1554
15. Felpin F.-X., Lebreton J. Tetrahedron Lett. 43:2002;225-227
16. For recent examples of metathesis-based synthesis from this laboratory, see: (a) Jo E., Na Y., Chang S. Tetrahedron Lett. 40:1999;5581-5582
17. Lee W.-W., Chang S. Tetrahedron: Asymmetry. 10:1999;4473-4475
18. Lee W.-W., Shin H.J., Chang S. Tetrahedron: Asymmetry. 12:2001;29-31
19. Park S.-H., Kang H.J., Ko S., Park S.Y., Chang S. Tetrahedron: Asymmetry. 12:2001;2621-2624
20. Chang S., Na Y., Shin H.J., Choi E., Jeong L.S. Tetrahedron Lett. 43:2002;7445-7448
21. Kang B., Kim D.-., Do Y., Chang S. Org. Lett. 5:2003;3041-3043
22. Tokunaga M., Larrow J.F., Kakiuchi F., Jacobsen E.N. Science. 277:1997;936-938
23. Jacobsen E.N. Acc. Chem. Res. 33:2000;421-431
24. Ready J.M., Jacobsen E.N. J. Am. Chem. Soc. 123:2001;2687-2688
25. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., Jacobsen E.N. J. Am. Chem. Soc. 124:2002;1307-1315
26. It was obtained in high enantiomeric purity (>98% ee) using the Jacobsen's protocol (Ref. 7) in multi gram scales from racemic epoxide
27. Lipshutz B.H., Wilhelm R.S., Kozlowski J.A. J. Org. Chem. 49:1984;3938-3942
28. Lipshutz B.H., Wilhelm R.S. J. Am. Chem. Soc. 103:1981;7672-7674
29. Smith J.G. Synthesis. 1984;629-656
30. Hoveyda A.H., Evans D.A., Fu G.C. Chem. Rev. 93:1993;1307-1370
31. Mihelich E.D., Daniels K., Eickhoff D.J. J. Am. Chem. Soc. 103:1981;7690-7692
32. Fringuelli F., Germani R., Pizzo F., Santinelli F., Savelli G. J. Org. Chem. 57:1992;1198-1202
33. Stork G., Takahashi T. J. Am. Chem. Soc. 99:1977;1275-1276
34. Greene T.W., Wuts P.G.M. 3rd ed. Protective Groups in Organic Synthesis. 1999;Wiley, New York
35. Seto H., Mander L.N. Synth. Commun. 22:1992;2823-2828
36. Yang W.-Q., Kitahara T. Tetrahedron. 56:2000;1451-1461. pp 27-33
37. Mitsunobu O. Synthesis. 1981;1-28
38. Edwards M.L., Stemerick D.M., McCarthy J.R. Tetrahedron Lett. 31:1990;3417-3420
39. Fukuyama T., Jow C.-K., Cheung M. Tetrahedron Lett. 36:1995;6373-6374
40. Nikam S.S., Kornberg B.E., Rafferty M.F. J. Org. Chem. 62:1997;3754-3757
41. For recent reviews on olefin metathesis, see: (a) Schuster M., Blechert S. Angew. Chem., Int. Ed. 36:1997;2036-2056
42. Grubbs R.H., Chang S. Tetrahedron. 54:1998;4413-4450
43. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012-3043
44. Connon S.J., Blechert S. Angew. Chem., Int. Ed. 42:2003;1900-1923
45. Grubbs R.H. Handbook of Metathesis. 2003;Wiley-VCH, Weinheim
46. Love J.A., Morgan J.P., Trnka T.M., Grubbs R.H. Angew. Chem., Int. Ed. 41:2002;4035-4037
47. For some selected examples of RCM using ammonium salts as a substrate, see: (a) Wright D.L., Schutle J.P. II, Page M.A. Org. Lett. 2:2000;1847-1850
48. Salim S.S., Bellingham R.K., Satcharoen V., Brown R.C.D. Org. Lett. 5:2003;3403-3406
49. Verhelst S.H.L., Martinez B.P., Timmer M.S.M., Lodder G., van der Marel G.A., Overkleeft H.S., van Boom J.H. J. Org. Chem. 68:2003;9598-9603
50. For some examples of tandem RCM and hydrogenation with a common ruthenium carbene precursor, see: (a) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312-11313
51. Sutton A.E., Seigal B.A., Finnegan D.F., Snapper M.L. J. Am. Chem. Soc. 124:2002;13390-13391
52. For some examples of tandem RCM and other catalytic reactions by the addition second catalysts, see: (a) Alexakis A., Croset K. Org. Lett. 4:2002;4147-4149
53. Cossy J., Bargiggia F., BouzBouz S. Org. Lett. 5:2003;459-462
54. Paquette L.A., Schloss J.D., Efremov I., Fabris F., Gallou F., Mendez-Andino J., Yang J. Org. Lett. 2:2000;1259-1261
55. Maynard H.D., Grubbs R.H. Tetrahedron Lett. 40:1999;4137-4140
56. Cho J.H., Kim B.M. Org. Lett. 5:2003;531-533
57. Ahn Y.M., Yang K.L., Georg G.I. Org. Lett. 3:2001;1411-1413
58. The calculated molarity of the m-chloroperbenzoic acid was based on the 77% purity of the commercial peracid