Preparation and reactions of 3,4-bis(tributylstannyl)-2(5H)-furanone

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 328-329

  Mabon, Ross ^a   Richecœur, Alexandre M E ^a   Sweeney, J B ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FURANONE DERIVATIVE; STANNYLSILYLFURANONE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0344075955     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9816156     Document Type: Article

References (23)

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5. For an overview, see: Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369. For treatises describing biological activities of cardenolides, see: Florkiewicz, R. Z.; Anchin, J.; Baird, A. J. Biol. Chem. 1998, 273, 544. Luta, M.; Hensel, A.; Kreis, W. Steroids 1998, 63, 44. Braga, F. C.; deSouzo, J. D.; Howarth, O.; deOliveira, A. B. Magn. Reson. Chem. 1997, 35, 899. Carter, C. A.; Gray, E. A.; Schneider, T. L.; Lovett, C. M.; Scott, L.; Messer, A. C.; Richardson, D. P. Tetrahedron 1997, 53, 16959. Gavidia, I.; PerezBermudez, P. Phytochemistry 1997, 46, 273. Florkiewicz, R. Z.; Anchin, J.; Trudel, C.; Baird, A. Mol. Biol. Cell 1996, 7, 1080.
6. For an overview, see: Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369. For treatises describing biological activities of cardenolides, see: Florkiewicz, R. Z.; Anchin, J.; Baird, A. J. Biol. Chem. 1998, 273, 544. Luta, M.; Hensel, A.; Kreis, W. Steroids 1998, 63, 44. Braga, F. C.; deSouzo, J. D.; Howarth, O.; deOliveira, A. B. Magn. Reson. Chem. 1997, 35, 899. Carter, C. A.; Gray, E. A.; Schneider, T. L.; Lovett, C. M.; Scott, L.; Messer, A. C.; Richardson, D. P. Tetrahedron 1997, 53, 16959. Gavidia, I.; PerezBermudez, P. Phytochemistry 1997, 46, 273. Florkiewicz, R. Z.; Anchin, J.; Trudel, C.; Baird, A. Mol. Biol. Cell 1996, 7, 1080.
7. For an overview, see: Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369. For treatises describing biological activities of cardenolides, see: Florkiewicz, R. Z.; Anchin, J.; Baird, A. J. Biol. Chem. 1998, 273, 544. Luta, M.; Hensel, A.; Kreis, W. Steroids 1998, 63, 44. Braga, F. C.; deSouzo, J. D.; Howarth, O.; deOliveira, A. B. Magn. Reson. Chem. 1997, 35, 899. Carter, C. A.; Gray, E. A.; Schneider, T. L.; Lovett, C. M.; Scott, L.; Messer, A. C.; Richardson, D. P. Tetrahedron 1997, 53, 16959. Gavidia, I.; PerezBermudez, P. Phytochemistry 1997, 46, 273. Florkiewicz, R. Z.; Anchin, J.; Trudel, C.; Baird, A. Mol. Biol. Cell 1996, 7, 1080.
8. For an overview, see: Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369. For treatises describing biological activities of cardenolides, see: Florkiewicz, R. Z.; Anchin, J.; Baird, A. J. Biol. Chem. 1998, 273, 544. Luta, M.; Hensel, A.; Kreis, W. Steroids 1998, 63, 44. Braga, F. C.; deSouzo, J. D.; Howarth, O.; deOliveira, A. B. Magn. Reson. Chem. 1997, 35, 899. Carter, C. A.; Gray, E. A.; Schneider, T. L.; Lovett, C. M.; Scott, L.; Messer, A. C.; Richardson, D. P. Tetrahedron 1997, 53, 16959. Gavidia, I.; PerezBermudez, P. Phytochemistry 1997, 46, 273. Florkiewicz, R. Z.; Anchin, J.; Trudel, C.; Baird, A. Mol. Biol. Cell 1996, 7, 1080.
9. For an overview, see: Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369. For treatises describing biological activities of cardenolides, see: Florkiewicz, R. Z.; Anchin, J.; Baird, A. J. Biol. Chem. 1998, 273, 544. Luta, M.; Hensel, A.; Kreis, W. Steroids 1998, 63, 44. Braga, F. C.; deSouzo, J. D.; Howarth, O.; deOliveira, A. B. Magn. Reson. Chem. 1997, 35, 899. Carter, C. A.; Gray, E. A.; Schneider, T. L.; Lovett, C. M.; Scott, L.; Messer, A. C.; Richardson, D. P. Tetrahedron 1997, 53, 16959. Gavidia, I.; PerezBermudez, P. Phytochemistry 1997, 46, 273. Florkiewicz, R. Z.; Anchin, J.; Trudel, C.; Baird, A. Mol. Biol. Cell 1996, 7, 1080.
10. For an overview, see: Marshal, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier: New York, 1970; Vol. II, Part D, p 369. For treatises describing biological activities of cardenolides, see: Florkiewicz, R. Z.; Anchin, J.; Baird, A. J. Biol. Chem. 1998, 273, 544. Luta, M.; Hensel, A.; Kreis, W. Steroids 1998, 63, 44. Braga, F. C.; deSouzo, J. D.; Howarth, O.; deOliveira, A. B. Magn. Reson. Chem. 1997, 35, 899. Carter, C. A.; Gray, E. A.; Schneider, T. L.; Lovett, C. M.; Scott, L.; Messer, A. C.; Richardson, D. P. Tetrahedron 1997, 53, 16959. Gavidia, I.; PerezBermudez, P. Phytochemistry 1997, 46, 273. Florkiewicz, R. Z.; Anchin, J.; Trudel, C.; Baird, A. Mol. Biol. Cell 1996, 7, 1080.
11. For a pertinent example, see: Staroske, T.; Hennig, I.; Wetzel, P.; Hofmann, H. J.; Muller, D.; Hausler, T.; Sheldrick, W. S.; Zillikens, S.; Gretzer, B.; Pusch, H.; Glitsch, H. G. Tetrahedron 1996, 52, 12723.
12. Piers, E.; Skerlj, R. T. Can. J. Chem. 1994, 72, 2468.
13. Searle, R. A.; Townsend, L. B. Org. Synth. 1981, 60, 81.
14. Mitchell, T. N.; Amamria, A.; Killing, H.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354.
15. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
16. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
17. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
18. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
19. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
20. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
21. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
22. Very few monocoupling reactions of unsymmetrical bisstannanes have been reported. For an example, see: (a) Beaudet, I.; Parrain, J.; Quintard, J.; Tetrahedron Lett. 1991, 32, 6333. Several selective single coupling reaction of symmetrical bisstananes have been reported: (b) Haack, R. A.; Penning, T. D.; Djuric, S. W.; Dziuba, J. A. Tetrahedron Lett. 1988, 29, 2783. (c) Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747. (d) Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. (e) Barrett, A. G. M.; Edmonds, J. J.; Hendrix, J. A.; Horita, K.; Parkinson, C. J. J. Chem. Soc., Chem. Commun. 1992, 1238. (f) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (g) Djuric, S. W.; Huff, R. M.; Penning, T. D.; Clare, M.; Swenton, L.; Kachur, J.; Vilani-Price, D.; Krivi, G. G.; Pyla, E. Y.; Warren, T. G. Bioorg. Med. Chem. Lett. 1992, 2, 1367. (h) Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 50, 9583.
23. Reginato, G.; Capperucci, A.; Degl'Innocenti, A.; Mordini, A.; Pecchi, S. Tetrahedron 1995, 51, 2129.