Stereoselective synthesis of 2,3,5-trisubstituted tetrahydrofurans by an allyl silane metathesis - Nucleophilic addition sequence

Synlett

Volumn , Issue 12, 1997, Pages 1411-1413

  Cassidy, John H ^a   Marsden, Stephen P ^a   Stemp, Geoffrey ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001806434     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1062     Document Type: Article

References (18)

1. Postema, M.H.D. C-Glycoside Synthesis; CRC: London, 1995.
2. Westley, J.W. Polyether Antibiotics: Naturally Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
3. For a recent review of the synthesis of 2,5-disubstituted tetrahydrofurans, see: Harmange, J.-C.; Figadere, B. Tetrahedron, Asymmetry 1993, 4, 1711.
4. For example, carbonyl ylide-olefin cycloaddition (Padwa, A; Fryxell, G.E.; Zhi, L. J. Am. Chem. Soc. 1990, 112, 3100);
5. trimethylenemethane-aldehyde condensation (Trost, B.M.; King, S.A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902);
6. allyl silane addition to aldehydes with silicon migration (Panek, J.S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868).
7. Masse, C.E.; Panek, J.S. Chem. Rev. 1995, 95, 1293.
8. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
9. Anhaus, J.T.; Gibson, V.C.; Clegg, W.; Collingwood, S.P. Organometallics 1993, 12, 1780.
10. Crowe, W.E.; Goldberg, D.R.; Zhang, Z.J. Tetrahedron Lett. 1996, 37, 2117.
11. Chang, S.B.; Grubbs, R.H. Tetrahedron Lett. 1997, 38, 4757.
12. The cyclisation precursors 1a-e were prepared by treatment of the homoallylic alcohols (from addition of allylmagnesium chloride to the appropriate aldehyde) with allyldimethylchlorosilane in DCM in the presence of triethylamine. Yields are in the range 77 to 79%.
13. 21OSi requires 233.1361.
14. 23O requires 231.1749.
15. Irradiation of the signal for H-2 gave enhancements of the signals for H-5 and H-3; irradiation of H-3 gave enhancements of the signals for H-2, H-5 and H-4a. Irradiation of H-5 gave enhancements of the signals for H-2, H-3, and H-4a. (Chemical Equation Presented)
16. Epimerisation of C-3 aldehydes of all-cis 2,3,5-trisubstituted tetrahydrofurans to the more stable 2,3-trans isomer is known. See, for example: Frauenrath, H.; Runsink, J. J. Org. Chem. 1987, 52, 2707.
17. Mohr, P. Tetrahedron Lett. 1993, 34, 6251.
18. Sano, T.; Oriyama, T. Synlett 1997, 716.