Template-directed intramolecular C-glycosidation. Stereoselective synthesis of bicyclic ketooxetanes from anomeric sulfones

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4153-4156

  Craig, Donald ^a   Tierney, Jason P ^a   Williamson, Christopher ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OXETANE DERIVATIVE; SULFONE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; GLYCOSYLATION; HYDROLYSIS; STEREOISOMERISM;

EID: 0031009882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00808-3     Document Type: Article

References (19)

1. Craig, D.; Munasinghe, V. R. N. J. Chem. Soc., Chem. Commun. 1993, 901-903.
2. Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1993, 34, 8539-8542; Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1995, 36, 5815-5818.
3. Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1993, 34, 8539-8542; Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1995, 36, 5815-5818.
4. Craig, D.; Munasinghe, V. R. N. Tetrahedron Lett. 1992, 33, 663-666.
5. For other intramolecular C-glycosidation reactions of tethered substrates, see: Martin, O. R.; Rao, S. P.; Kurz, K. G.; Elshenawy, H. A. J. Am. Chem. Soc. 1988, 110, 8698-8700; Martin, O. R. Carbohydr. Res. 1987, 171, 211-222.
6. For other intramolecular C-glycosidation reactions of tethered substrates, see: Martin, O. R.; Rao, S. P.; Kurz, K. G.; Elshenawy, H. A. J. Am. Chem. Soc. 1988, 110, 8698-8700; Martin, O. R. Carbohydr. Res. 1987, 171, 211-222.
7. 13C nmr and ir spectra, and which showed low-resolution ms and either elemental combustion analysis or high-resolution ms characteristics in accord with the assigned structures.
8. Dyatkina, N. B.; Azhayev, A. V. Synthesis 1984, 961-963.
9. An adaptation of Williams' method was employed: Stewart, A. O.; Williams, R. M.;J. Am. Chem. Soc. 1985, 107, 4289-4296.
10. We have not assigned the major and minor S-glycoside anomers.
11. Mercuric acetate, mercuric trifluoroacetate and zinc chloride all failed to initiate the desired cyclisation.
12. Tanis, S. P.; Robinson, E. D.; McMills, M. C.; Watt, W. J. Am. Chem. Soc. 1992, 114, 8349-8362, and references therein.
13. Brown, D. S.; Ley, S. V.; Vile, S.; Thompson, M. Tetrahedron 1991, 47, 1329-1342, and references cited therein.
14. Emde, H.; Domsch, D.; Feger, H.; Frick, U.; Götz, A.; Hergott, H. H.; Hofmann, K.; Kober, W.; Krägeloh, K.; Oesterle, T.; Steppan, W.; West, W.; Simchen, G. Synthesis 1982, 1-26. Enol ethers 5 and 6 both were formed exclusively as the Z-isomers.
15. - on the anomeric cation in a fashion anti with respect to the neighbouring α-ketonic group.
16. Mori, M.; Nishide, Y.; Ohrui, H.; Heguro, H. J. Org. Chem. 1989, 54, 1346-1353.
17. Compound 13 was prepared from D-galactopyranose in 53% yield by treatment with TIPS-Cl and imidazole in DMF (1M) containing 10 mol % DMAP (rt, 29 h).
18. 3PO from the activated lactol, allowing formation of the anomerically stabilised α-stereoisomer.
19. We thank Professor David J. Williams and Dr Andrew J. P. White of this Department for the X-ray structure determination.