Fluoride-assisted regioselective conversion of functionalized furans to α-substituted γ-hydroxybutenolides using singlet oxygen

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6305-6308

  Patil, Santoshkumar N ^a   Liu, Fei ^a  

^a MACQUARIE UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE; FURAN RESINS; OXYGEN; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

BAYLIS-HILLMAN REACTION; FURANS; TBAF;

OLEFINS;

BUTENOLIDE; FLUORIDE; FURAN DERIVATIVE; SINGLET OXYGEN;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL MODIFICATION; OXIDATION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

4-BUTYROLACTONE; CATALYSIS; CHEMISTRY, ORGANIC; FLUORIDES; FURANS; MODELS, CHEMICAL; OXYGEN; QUATERNARY AMMONIUM COMPOUNDS; SINGLET OXYGEN; STEREOISOMERISM;

EID: 34547644884     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070666c     Document Type: Article

References (14)

1. For recent examples of α- or β-substituted bioactive butenolides found in nature, see: (a) Wright, A. D.; Nys, R. D.; Angerhofer, C. K.; Pezzuto, J. M.; Gurrath, M. J. Nat. Prod. 2006, 69, 1180-1187.
2. (b) Keyzers, R. A.; Davies-Coleman, M. T. Chem. Soc. Rev. 2005, 34, 355-365.
3. (c) Charan, R. D.; McKee, T. C.; Boyd, M. R. J. Org. Chem. 2001, 64, 661-663.
4. For recent reviews of synthetic routes to butenolides, see: (a) Brückner, R. Curr. Org. Chem. 2001, 5, 679-718.
5. (b) Carter, N. B.; Nadany, A. E.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 2002, 2324-2342.
6. For initial work in photooxidative conversion of furans to γ-hydroxybutenolides, see: (a) Grimminger, W.; Kraus, W. Lieb. Ann. Chem. 1979, 10, 1571-1576.
7. (b) Brownbridge, P.; Chan, T. H. Tetrahedron Lett. 1980, 21, 3431-3434.
8. (c) Katsumura, S.; Hori, K.; Fugiwara, S.; Isoe, S. Tetrahedron Lett. 1985, 26, 4625-4628.
9. (d) Kernan, M. R.; Faulkner, D. J. J. Org. Chem. 1988, 53, 2773-2776.
10. For a recent summary of the use of singlet oxygen in biomimetic syntheses, see: (e) Margaros, I.; Montagnon, T.; Tofi, M.; Pavlakos, E.; Vassilikogiannakis, G. Tetrahedron 2006, 62, 5308-5317.
11. For a very recent example of regioselective synthesis of γ-hydroxybutenolides, see: (f) Aquino, M.; Bruno, I.; Riccio, R.; Gomez-Paloma, L. Org. Lett. 2006, 8, 4831-4834.
12. Patil, S. N.; Liu, F. Org. Lett. 2007, 9, 195-198.
13. Ma, S.; Lu, L.; Lu, P. J. Org. Chem. 2005, 70, 1063-1065.
14. Kaburagi, Y.; Kishi, Y. Org. Lett. 2007, 9, 723-726.