Cobalt-assisted Claisen rearrangement of enediyne lactones at ambient temperature. Studies toward a synthetic application of the Myers cycloaromatization

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4848-4852

  Vourloumis, Dionisios ^a   Kim, Kee D ^a   Petersen, Jeffrey L ^a   Magriotis, Plato A ^a,b  

^a HARVARD UNIVERSITY   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029946059     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9520506     Document Type: Article

References (46)

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3. For reviews describing mechanistic, synthetic, and DNA-cleaving studies of neocarzinostatin, calicheamicin, esperamicin, and dynemicin, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (c) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (d) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH Publishers, Inc.: New York, 1995; pp 203-283.
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28. For specific data see the supporting information.
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30. For control of ketene acetal geometry in esters, see: (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D., III. J. Org. Chem. 1991, 56, 650. (c) Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572. (d) Hattori, K.; Yamamoto, H. Tetrahedron 1994, 50, 3099.
31. For control of ketene acetal geometry in esters, see: (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D., III. J. Org. Chem. 1991, 56, 650. (c) Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572. (d) Hattori, K.; Yamamoto, H. Tetrahedron 1994, 50, 3099.
32. For control of ketene acetal geometry in esters, see: (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D., III. J. Org. Chem. 1991, 56, 650. (c) Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572. (d) Hattori, K.; Yamamoto, H. Tetrahedron 1994, 50, 3099.
33. For precedent on selective complexation of enediynes, see: Magnus, P.; Carter, P.; Elliott, J.; Lewis, R.; Harling, J.; Pitterna, T.; Bauta, W. E.; Fortt, S. J. Am. Chem. Soc. 1992, 114, 2544 and earlier work.
34. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
35. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
36. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
37. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
38. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
39. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
40. For an excellent recent review of the Claisen rearrangement, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry; 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; G. Theime: Stuttgart, 1995; Vol. E 21d, pp 3301-3547. For key papers on the lactonic variation of the Ireland-Claisen process, see: (a) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6889. (b) Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chern. Soc. 1982, 104, 4030. (c) Cameron, A. G.; Knight, D. W. Tetrahedron Lett. 1982, 23, 5455. (d) Brunner, R. K.; Borachberg, H.-J. Helv. Chim. Acta 1983, 66, 2608. (e) Reference 4. (f) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229.
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44. The author has deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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