Synthesis of diastereomerically pure indolizidine and pyrrolizidine analogues from D-pentoses

Tetrahedron Asymmetry

Volumn 8, Issue 19, 1997, Pages 3223-3230

  Marek, Delphine ^a   Wadouachi, Anne ^a   Beaupère, Daniel ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030821784     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00427-8     Document Type: Article

References (17)

1. Burgess, K.; Henderson, I. Tetrahedron, 1992, 48, 4045-4066.
2. Marek, D.; Wadouachi, A.; Uzan, R.; Beaupère, D. Tetrahedron Lett., 1996, 37, 49-52.
3. Clissod, D. W., UK Patent, 1987, 2188626A.
4. Kartha, K. P. R. Tetrahedron Lett., 1986, 27, 3415-3416.
5. Collins, P. M. in Carbohydrates, Ed.; Chapman and Hall/London, 1987.
6. Eliel, E. L.; Wilen, S. H. in Stéréochimie des Composés Organiques, Ed.; Lavoisier, 1996, p. 628.
7. Collins, P.; Ferrier, R. in Monosaccharides, Ed.; Wiley, J., 1995, p. 116.
8. Helferich, B. Adv. Carbohydr. Chem., 1948, 3, 79-111. Introduction of trityl group at C5 hydroxyl group was realized by treatment of pentose (1 eq.) with trityl chloride (1.4 eq.) in pyridine. The mixture was stirred for 24 h, then concentrated under reduced pressure and the crude product chromatographed on silica gel (hexane-ethylacetate 8:2).
9. 13 afforded two regioisomers: the 2,3-O-isopropylidene-and the 3,4-O-isopropylidene-D-xylopyranosyl benzoate isolated in 40% and 10% yield respectively. Deprotection of the anomeric hydroxyl group was realized by treatment with sodium methoxide to give quantitatively 23 and 26.
10. (a) Mitsunobu, O. Synthesis 1981.
11. (b) Bernotas, R. C.; Cube, R. V. Tetrahedron Lett., 1991, 32, 161-164.
12. Martin, O. R.; Saavedra, O. M. Tetrahedron Lett., 1995, 36, 799-802.
13. (a) Larabi, M. L. Halogénation et azidation régiosélectives directes d'aldoses non protégés, Université de Picardie Jules Verne, 1994.
14. (b) Larabi, M. L.; Fréchou, C.; Demailly, G. Carbohydr. Lett., 1996, 2, 61-66.
15. (a) Debost, J. L.; Gelas, J.; Horton, D.; Mols, O. Carbohydr. Res., 1984, 125, 329-335.
16. (b) Cai, J.; Davison; B. E.; Ganelli, R.; Thaisrivongs, S. Tetrahedron Lett., 1995, 36, 6535-6536.
17. Cramer, F. D. in Methods in Carbohydr. Chem., 1963, 2, 244-245.