Synthesis of new chiral mixed cis-tetraheterodecalines by highly selective cyclization of N,N′-bisalkyl 2,3-diaminobutanediols

Synthesis

Volumn , Issue 7, 2006, Pages 1093-1098

  Gras, Jean Louis ^a   Taulier, Eric ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Amino alcohols; Fused ring systems; Heterocycles; Ring closure

Indexed keywords

ALCOHOLS; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

AMINO ALCOHOLS; FUSED-RING SYSTEMS; HETEROCYCLES; RING CLOSURES;

AMINES;

2,3 BUTANEDIOL; 2,7 DIAZA 4,9 DIOXA[4.4.0]DECANE DERIVATIVE; ALKYL GROUP; DECALIN DERIVATIVE; DECANE; DIAMINE; DIOXANE DERIVATIVE; TARTARIC ACID; TETRAHETERODECALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIS TRANS ISOMERISM; CYCLIZATION; SYNTHESIS;

EID: 33645987632     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926389     Document Type: Article

References (29)

1. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580.
2. 2-symmetric ligands: (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
3. (b) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
4. Hirama, M.; Oishi, T.; Itô, S. J. Chem. Soc., Chem. Commun. 1989, 665.
5. Helmchen, G.; Krotz, A.; Ganz, K.-T.; Hansen, D. Synlett 1991, 257.
6. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
7. Muller, D.; Umbricht, G.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
8. (a) Feit, P. W.; Nielsen, O. T. J. Med. Chem. 1967, 10, 697.
9. (b) Feit, P. W.; Nielsen, O. T. J. Med. Chem. 1970, 13, 447.
10. (c) Haines, A. H.; Morley, C.; Murrer, B. A. J. Med. Chem. 1989, 32, 742.
11. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880.
12. Lee, S.-g.; Lim, C. W.; Song, C. E.; Okim, I.; Jun, C.-H. Tetrahedron: Asymmetry 1997, 8, 2927.
13. Tanner, D.; Railton, C. J.; Pettersson, I.; Sotofte, I. Acta Chem. Scand. 1999, 53, 703.
14. Lee, S.-g.; Lim, C. W.; Song, C. E.; Kim, K. M.; Jun, C.-H. J. Org. Chem. 1999, 64, 4445.
15. (a) Gras, J.-L.; Pellisier, H.; Nouguier, R. J. Org. Chem. 1989, 54, 5675.
16. (b) Gras, J.-L.; Pellisier, H. Tetrahedron 1991, 32, 7043.
17. (c) Gras, J.-L.; Dulphy, H.; Lejon, T. Tetrahedron 1996, 52, 8517.
18. (d) Gras, J.-L.; Soto, T.; Viala, J. Tetrahedron: Asymmetry 1997, 8, 3829.
19. Gras, J.-L.; Dulphy, H.; Lejon, T. Bull. Soc. Chim. Fr. 1994, 737,418.
20. Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1422.
21. Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875.
22. Star, A.; Lemcoff, G.; Goldberg, I.; Fuchs, B. Tetrahedron Lett. 1997, 38, 3573.
23. Oishi, T.; Hirama, M. Tetrahedron Lett. 1992, 33, 639.
24. Scheuren, A.; Mosset, P.; Saalfranck, R. W. Tetrahedron: Asymmetry 1999, 10, 3559.
25. Star, A.; Lemcoff, G.; Goldberg, I.; Lemcoff, N. G.; Fuchs, B. Eur. J. Org. Chem. 1999, 2033.
26. Roberts, J. J.; Ross, W. C. J. Chem. Soc. 1952, 4288.
27. Agami, C.; Rizk, T. Tetrahedron 1985, 41, 537.
28. Riddell, F. G.; Lehn, J.-M. J. Chem. Soc., B 1968, 1224.
29. Perrin, D. D.; Armengo, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.