Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose

Carbohydrate Research

Volumn 343, Issue 10-11, 2008, Pages 1675-1692

  Cumpstey, Ian ^a   Gehrke, Sebastian ^a   Erfan, Sayeh ^a   Cribiu, Riccardo ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

l Sorbose; Ring closing metathesis; Valienamine

Indexed keywords

CARBOHYDRATES; GLUCOSE; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CARBOCYCLIC PRECURSOR; L-SORBOSE; RING CLOSING METATHESIS; VALIENAMINE;

AMINES;

1 EPI VALIENAMINE; 2,3,4 TRI O BENZYL 5 (BENZYLOXYMETHYL)CYCLOHEX 5 ENE 1,2,3,4 TETROL; AMINE; CYCLOHEXENE DERIVATIVE; GLUCOSE; NITROGEN; SORBOSE; VALIENAMINE;

ARTICLE; CHEMICAL STRUCTURE; PRECURSOR; PRIORITY JOURNAL; RING CLOSING METATHESIS; SYNTHESIS;

CYCLOHEXENES; GLUCOSE; HEXOSAMINES; SORBOSE; STEREOISOMERISM;

EID: 46549089189     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.04.010     Document Type: Article

References (40)

1. Chen X., Fan Y., Zheng Y., and Shen Y. Chem. Rev. 103 (2003) 1955-1977
2. Arjona O., Gomez A.M., Lopez J.C., and Plumet J. Chem. Rev. 107 (2007) 1919-2036
3. Ogawa S. Trends Glycosci. Glyc. 16 (2004) 33-53
4. Akhtar, T.; Eriksson, L.; Cumpstey, I. Carbohydr. Res., in press, doi:10.1016/j.carres.2008.01.013.
5. Akhtar T., and Cumpstey I. Tetrahedron Lett. 48 (2007) 8673-8677
6. Cumpstey I. Synlett (2006) 1711-1714
7. Kapferer P., Sarabia F., and Vasella A. Helv. Chim. Acta 82 (1999) 645-656
8. Madsen R. Eur. J. Org. Chem. (2007) 399-415
9. Cumpstey I. Tetrahedron Lett. 46 (2005) 6257-6259
10. Whalen L.J., and Halcomb R.L. Org. Lett. 6 (2004) 3221-3224
11. Chang Y.-K., Lee B.-Y., Kim D.J., Lee G.S., Jeon H.B., and Kim K.S. J. Org. Chem. 70 (2005) 3299-3302
12. Wang Y., and Bennet A.J. Org. Biomol. Chem. 5 (2007) 1731-1738
13. Kornienko A., and D'Alarcao M. Tetrahedron: Asymmetry 10 (1999) 827-829
14. Andresen T.L., Skytte D.M., and Madsen R. Org. Biomol. Chem. (2004) 2951-2957
15. Cram D.J., and Kopecky K.R. J. Am. Chem. Soc. 81 (1959) 2748-2755
16. Mengel A., and Reiser O. Chem. Rev. 99 (1999) 1191-1223
17. Marco-Contelles J., de Opazo E., and Arroyo N. Tetrahedron 57 (2001) 4729-4739
18. Cribiu R., and Cumpstey I. Chem. Commun. (2008) 1246-1248
19. Seepersaud M., and Al-Abed Y. Tetrahedron Lett. 41 (2000) 7801-7803
20. Rambaud L., Compain P., and Martin O.R. Tetrahedron: Asymmetry 12 (2001) 1807-1809
21. Flamme E.M., and Roush W.R. Beilstein J. Org. Chem. 1 (2005) 7
22. Gomez A.M., Moreno E., Valverde S., and Lopez J.C. Tetrahedron Lett. 43 (2002) 7863-7866
23. Aurrecoechea J.M., Arrate M., and López B. Synlett (2001) 872-874
24. Prepared according to:. Howell S.J., Spencer N., and Philp D. Tetrahedron 57 (2001) 4945-4954
25. Hayashida M., Sakairai N., and Kuzuhara H. Carbohydr. Res. 154 (1986) 115-126
26. Fukase H., and Horii S. J. Org. Chem. 57 (1992) 3651-3658
27. Cipolla L., Lay L., Nicotra F., Pangrazio C., and Panza L. Tetrahedron 51 (1995) 4679-4690
28. Cipolla L., La Ferla B., Peri F., and Nicotra F. J. Chem. Soc., Chem. Commun. (2000) 1289-1290
29. Cipolla L., Palma A., La Ferla B., and Nicotra F. J. Chem. Soc., Perkin Trans. 1 (2002) 2161-2165
30. Balan D., and Adolfsson H. Tetrahedron Lett. 45 (2004) 3089-3092
31. Neimert-Andersson K., and Somfai P. Eur. J. Org. Chem. 71 (2006) 978-985
32. Marco-Contelles J., and de Opazo E. J. Org. Chem. 65 (2000) 5416-5419
33. Marco-Contelles J., and de Opazo E. J. Org. Chem. 67 (2002) 3705-3717
34. Boyer F.-D., and Hanna I. Tetrahedron Lett. 42 (2001) 1275-1277
35. Nicotra F., Panza L., Ronchetti F., and Russo G. Gazz. Chim. Ital. 119 (1989) 577-579
36. Lichtenthaler F.W., and Mondel S. Pure Appl. Chem. 69 (1997) 1853-1866
37. Lichtenthaler F.W. Carbohydr. Res. 313 (1998) 69-89
38. Shi Y. Organocatalytic Oxidation. Ketone-Catalyzed Asymmetric Epoxidation of Olefins. In: Bäckvall J.-E. (Ed). Modern Oxidation Methods (2005), Wiley-VCH 51-82
39. Helleur R., Rao V.S., and Perlin A.S. Carbohydr. Res. 89 (1981) 83-90
40. Taber D.F., and Frankowski K.J. J. Org. Chem. 68 (2003) 6048-6049