Furanyl spiroketals: thermodynamic control of remote asymmetry

Tetrahedron Letters

Volumn 47, Issue 22, 2006, Pages 3665-3668

  Cahill, Shane ^a   O'Brien, Matthew ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Anomeric effect; Furanyl ethers; Remote asymmetry; Spiroketals

Indexed keywords

ACETAL DERIVATIVE; ALKYNE DERIVATIVE; LACTONE DERIVATIVE; LITHIUM ACETATE;

ARTICLE; CYCLIZATION; DESILYLATION; DIASTEREOISOMER; EQUILIBRIUM CONSTANT; HYDROGENATION; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 33646486722     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.135     Document Type: Article

References (26)

1. For reviews see:. Mead K.T., and Brewer B.N. Curr. Org. Chem. 7 (2003) 227-256
2. Perron P., and Albizati K.F. Chem. Rev. 89 (1989) 1617-1661
3. Fletcher M.T., and Kitching W. Chem. Rev. 95 (1995) 789-828
4. Francke W., and Kitching W. Curr. Org. Chem. 5 (2001) 233-251
5. Deslongchamps P., Pothier N., and Goldstein S. Helv. Chim. Acta 75 (1992) 604-620
6. Murata M., and Yasumoto T. Nat. Prod. Rep. 17 (2000) 293-314
7. Uckun F.M., Mao C., Vassilev A.O., Haung H., and Jan S.-T. Bioorg. Med. Chem. Lett. 10 (2000) 541-545
8. Danishefsky S.J., DeNinno S., and Lartey P. J. Am. Chem. Soc. 109 (1987) 2082-2089
9. Maeha I., Iwata K., Usami F., and Furukawa H. J. Org. Chem. 48 (1983) 2998-3002
10. For recent syntheses involving this approach see:. Allen P.R., and Brimble M.A. J. Chem. Soc., Perkin Trans. 1 (1998) 2403-2412
11. Shimazu T., Kusaka J., Ishiyama H., and Nakata T. Tetrahedron Lett. 44 (2003) 4965-4968
12. Dounay A.B., Urbanek R.A., Frydrychowski V.A., and Forsyth C.J. J. Org. Chem. 66 (2001) 925-938
13. Tu Y.Q., Hubener A., Zhang H., Moore C.J., Fletcher M.T., Hayes P., Dettner K., Francke W., McErlean C.S.P., and Kitching W. Synthesis 13 (2000) 1956-1978
14. Doubsky D., Streinz L., Saman D., Zednik J., and Koutek B. Org. Lett. 6 (2004) 4909
15. Schwartz B.D., Hayes P.Y., Kitching W., and De Voss J.J. J. Org. Chem. 70 (2005) 3054-3065
16. Bieber L.W., da Silva M.F., da Costa R.C., and Silva L.O.S. Tetrahedron Lett. 39 (1998) 3655-3658
17. Petrier C., and Luche J.-L. J. Org. Chem. 50 (1985) 910-912
18. Lubineau A., Auge J., and Queneau Y. Synthesis (1994) 741-760
19. Makoto H., Sakuragi R., Okabe S., and Hosomi A. Chem. Commun. (2001) 357-358
20. Brown H.C., Khire U.R., Narla G., and Racherla U.S. J. Org. Chem. 60 (1995) 545-549
21. 3: 293.2117].
22. Carlsen P.H.J., Katsuki T., Martin V.S., and Sharpless K.B. J. Org. Chem. 46 (1981) 3936-3938
23. Gschwend H.W., and Rodriguez H.R. Org. React. 26 (1979) 1-360
24. Achmatowicz Jr. O., Bukowski P., Szechner B., Zwierzchowska Z., and Zamojski A. Tetrahedron 27 (1971) 1973-1996
25. Kobayashi Y., Nakano M., Kumar G.B., and Kishihara K. J. Org. Chem. 63 (1998) 7505-7515
26. Kappe C.O., Murphree S.S., and Padwa A. Tetrahedron 53 (1997) 14179-14233