Synthesis of new furan derivatives and 4-hydroxy aldehydes from 4-hydroxy 1-enol ethers

Synthesis

Volumn , Issue 12, 2004, Pages 1963-1970

  Hölemann, Alexandra ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

lactols; lactones; Aldehydes; Enol ethers; Tetrahydrofuran derivatives

Indexed keywords

FURAN DERIVATIVES; LEWIS ACID;

ALCOHOLS; FURAN RESINS; HYDROLYSIS; ORGANIC ACIDS; OXIDATION;

ETHERS;

ALDEHYDE DERIVATIVE; CHROMIC ACID; ETHER DERIVATIVE; FURAN DERIVATIVE; GAMMA LACTONE DERIVATIVE; PYRIDINIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; HYDROLYSIS; OXIDATION; SILYLATION; SYNTHESIS;

EID: 4444252817     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829175     Document Type: Article

References (39)

1. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
2. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
3. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
4. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
5. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
6. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
7. Reviews: (a) Elliot, M. C. J. Chem. Soc., Perkin Trans, 1 1998, 4175. (b) Koert, U. Synthesis 1995, 115. (c) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Mori, K. Tetrahedron 1989, 45, 3233. (f) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (g) Westley, J. W. Polyether Antibiotics: Natural Occurring Acid Ionophores; Marcel Dekker: New York, 1982.
8. (a) Hölemann, A.; Reissig, H.-U. Org. Lett. 2003, 5, 1463.
9. (b) Hölemann, A.; Reissig, H.-U. Chem.-Eur. J. 2004, 10, in press.
10. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
11. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
12. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
13. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
14. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
15. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
16. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
17. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
18. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
19. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Molander, G. A. Chem. Rev. 1992, 92, 29. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (d) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Lavai, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans, 1 2001, 2727. (h) Hölemann, A. Synlett 2001, 1497. (i) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (j) Kagan, H. B. Tetrahedron 2003, 59, 10351.
20. Selected recent references on samarium diiodide-induced ketyl-olefin coupling reactions: (a) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422. (b) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872.
21. Selected recent references on samarium diiodide-induced ketyl-olefin coupling reactions: (a) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422. (b) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872.
22. Selected recent references on samarium diiodide-induced ketyl-olefin coupling reactions: (a) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422. (b) Schmalz, H.-G.; Kiehl, O.; Gotov, B. Synlett 2002, 1253. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872.
23. Gillmann, T. Tetrahedron Lett. 1993, 34, 607.
24. (a) Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1998, 63, 3701.
25. (b) Bruckner, C.; Reissig, H.-U. J. Org. Chem. 1988, 53, 2440.
26. (a) Schmitt, A.; Reissig, H.-U. Eur. J. Org. Chem. 2001, 1169.
27. (b) Schmitt, A.; Reissig, H.-U. Eur. J. Org. Chem. 2000, 3893.
28. (c) Schmitt, A.; Reissig, H.-U. Synlett 1990, 40.
29. (d) Schmitt, A.; Reissig, H.-U. Chem. Ber. 1995, 128, 871.
30. (e) Brückner, C.; Holzinger, H.; Reissig, H.-U. J. Org. Chem. 1988, 53, 2450.
31. (a) Smith, D. M.; Tran, M. B.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 14149.
32. (b) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208.
33. (c) Shaw, J. T.; Woerpel, K. A. Tetrahedron 1999, 55, 8747.
34. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 5321.
35. Takayama, H.; Koike, T.; Aimi, N.; Sakai, S. J. Org. Chem. 1992, 57, 2173.
36. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324.
37. Gerlach, H.; Künzler, P. Helv. Chim. Acta 1978, 61, 2503.
38. Taylor, S. K.; Chmiel, N. H.; Mann, E. E.; Silver, M. E.; Vyvyan, J. R. Synthesis 1998, 1009.
39. Davies, D. H.; Haire, N. A.; Hall, J.; Smith, E. H. Tetrahedron 1992, 48, 7839.