Stereoselective synthesis of 3,4-disubstituted tetrahydrofurans and 2,3,4-trisubstituted tetrahydrofurans using an intramolecular allylation strategy employing allylsilanes

Tetrahedron Letters

Volumn 49, Issue 16, 2008, Pages 2514-2518

  Jervis, Peter J ^a   Kariuki, Benson M ^a   Cox, Liam R ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Allylsilanes; Br nsted acids; Cyclisation; Intramolecular allylation; Tetrahydrofurans

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; AUREONITOL; BRONSTED ACID; GYNUNONE; JASPINE B; NATURAL PRODUCT; SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG STRUCTURE; MOLECULAR DYNAMICS; QUANTUM YIELD; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 40849114386     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.088     Document Type: Article

References (34)

1. Sefkow M. Top. Curr. Chem. 243 (2005) 185-224
2. Hoppe R., and Scharf H.-D. Synthesis (1995) 1447-1464
3. Kuroda I., Musman M., Ohtani I.I., Ichiba T., Tanaka J., Gravalos D.G., and Higa T. J. Nat. Prod. 65 (2002) 1505-1506
4. Ledroit V., Debitus C., Lavaud C., and Massiot G. Tetrahedron Lett. 44 (2003) 225-228
5. For a recent synthesis see:. Passiniemi M., and Koskinen A.M.P. Tetrahedron Lett. 49 (2008) 980-983
6. Lin W.-Y., Teng C.-M., Tsai I.-L., and Chen I.-S. Phytochemistry 53 (2000) 833-836
7. Bohlmann F., and Ziesche J. Phytochemistry 18 (1979) 664-665
8. Abraham W.R., and Arfmann H.A. Phytochemistry 18 (1992) 2405-2408
9. see also:. Marwah R.G., Fatope M.O., Deadman M.L., Al-Maqbali Y.M., and Husband J. Tetrahedron 63 (2007) 8174-8180
10. Ramalho R., Jervis P.J., Kariuki B.M., Humphries A.C., and Cox L.R. J. Org. Chem. 73 (2008) 1631-1634
11. Jervis P.J., and Cox L.R. Beilstein J. Org. Chem. 3 (2007) 6
12. Jervis P.J., Kariuki B.M., and Cox L.R. Org. Lett. 8 (2006) 4649-4652
13. Ramalho R., Beignet J., Humphries A.C., and Cox L.R. Synthesis (2005) 3389-3397
14. Beignet J., Tiernan J., Woo C.H., Kariuki B.M., and Cox L.R. J. Org. Chem. 69 (2004) 6341-6356
15. Beignet J., and Cox L.R. Org. Lett. 5 (2003) 4231-4234
16. For other recent approaches see:. Wolfe J.P., and Hay M.B. Tetrahedron 63 (2007) 261-290
17. Reddy L.V.R., Roy A.D., Roy R., and Shaw A.K. Chem. Commun. (2006) 3444-3446
18. Nasveschuk C.G., Jui N.T., and Rovis T. Chem. Commun. (2006) 3119-3121
19. Yoda H., Kimura K., and Takabe K. Synlett (2001) 400-402
20. Angle S.R., Bernier D.S., Chann K., Jones D.E., Kim M., Neitzel M.L., and White S.L. Tetrahedron Lett. 39 (1998) 8195-8198
21. Bonini C., Esposito V., D'Auria M., and Righi G. Tetrahedron 53 (1997) 13419-13426
22. Evans D.A., Dart M.J., Duffy J.L., and Yang M.G. J. Am. Chem. Soc. 118 (1996) 4322-4343
23. Evans D.A., Duffy J.L., and Dart M.J. Tetrahedron Lett. 35 (1994) 8537-8540
24. Evans D.A., Dart M.J., and Duffy J.L. Tetrahedron Lett. 35 (1994) 8541-8544
25. Iversen T., and Bundle D.R. J. Chem. Soc., Chem. Commun. (1981) 1240-1241
26. Clark J.S., Fessard T.C., and Wilson C. Org. Lett. 6 (2004) 1773-1776
27. We have found the use of 0.1 equiv of TMSOTf to be more effective than our previously described approach (see Ref. 6c) using stoichiometric TMSOTf in the presence of a Brønsted acid scavenger.
28. Use of Lindlar catalyst led to appreciable amounts of over-reduction.
29. The over-reduction product was not separated from the desired allylsilane but was readily separable from the tetrahydrofuran cyclisation products.
30. +), 151 (100), 121 (25), 106 (89), 92 (14), 84 (45), 77 (15), 56 (24), 44 (5).
31. 2 requires 190.9940.
32. Crystallographic data (excluding structure factors) for the structures in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications nos. 10f CCDC 677099; 12c CCDC 677098; 14 CCDC 677100. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
33. Brinza I.M., and Fallis A.G. J. Org. Chem. 61 (1996) 3580-3581
34. Cornforth J.W., Cornforth R.H., and Mathew K.K. J. Chem. Soc. (1959) 112-127