Rearrangement of 2-dienylcyclobutenones. Synthesis of highly substituted annulated furans

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2584-2585

  Turnbull, Philip ^a   Heileman, Matthew J ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030005350     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952247y     Document Type: Article

References (19)

1. (a) Perri, S. T.; Poland, L. D.; Decker, O. H. W.; Moore, H W. J. Org. Chem. 1986, 51, 8067.
2. (b) Liebeskind, L. S.; Jewell, C. F.; Iyer, S. J. Org. Chem. 1986, 51, 3065.
3. For reviews on the ring expansions of cyclobutenones see: (a) Moore, H. W ; Yerxa, B. R. Chemtracts 1992, 5, 273. (b) Liebeskind, L. S. Tetrahedron 1989, 45, 3053. (c) Bellus, D.; Ernst, B. Angew Chem. 1988, 100, 820
4. For reviews on the ring expansions of cyclobutenones see: (a) Moore, H. W ; Yerxa, B. R. Chemtracts 1992, 5, 273. (b) Liebeskind, L. S. Tetrahedron 1989, 45, 3053. (c) Bellus, D.; Ernst, B. Angew Chem. 1988, 100, 820
5. For reviews on the ring expansions of cyclobutenones see: (a) Moore, H. W ; Yerxa, B. R. Chemtracts 1992, 5, 273. (b) Liebeskind, L. S. Tetrahedron 1989, 45, 3053. (c) Bellus, D.; Ernst, B. Angew Chem. 1988, 100, 820
6. Houk, K N.; Rondan, N. G. J. Am. Chem. Soc. 1985, 107, 2099.
7. The concept of vinylketene/cyclobutenone equilibrium is supported by the following works: (a) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 644. (b) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 776, 9471.
8. The concept of vinylketene/cyclobutenone equilibrium is supported by the following works: (a) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 644. (b) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 776, 9471.
9. This reduction method was adopted from a similar example: Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897.
10. For examples of conjugate additions to ethenylcyclobutenones see: (a) Xu, S.: Yerxa, B. R., Sullivan, R. W.; Moore, H. W. Tetrahedron Lett. 1991, 32, 1129. (b) Liu, H.; Gayo, L. M.: Sullivan, R. W.; Choi, A. Y. H.; Moore, H. W. J. Org. Chem. 1994, 53, 3284.
11. For examples of conjugate additions to ethenylcyclobutenones see: (a) Xu, S.: Yerxa, B. R., Sullivan, R. W.; Moore, H. W. Tetrahedron Lett. 1991, 32, 1129. (b) Liu, H.; Gayo, L. M.: Sullivan, R. W.; Choi, A. Y. H.; Moore, H. W. J. Org. Chem. 1994, 53, 3284.
12. For a good review of the synthetic utility of copper reagents see: Lipshutz, B. H.; Sengupta, S. Org. React. (New York) 1992, 41, 135.
13. For other methods of synthesizing highly substituted cyclobutenones see. (a) Liebeskind, L. S.; Fengl, R. W ; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482 (b) Gayo, L. M.; Winters, M. P.; Moore, H. W J. Org. Chem. 1992, 57, 6896. (c) Edwards, J. P.; Krysan, D. J.; Liebeskind, L. S. J. Org. Chem. 1993, 58, 3942.
14. For other methods of synthesizing highly substituted cyclobutenones see. (a) Liebeskind, L. S.; Fengl, R. W ; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482 (b) Gayo, L. M.; Winters, M. P.; Moore, H. W J. Org. Chem. 1992, 57, 6896. (c) Edwards, J. P.; Krysan, D. J.; Liebeskind, L. S. J. Org. Chem. 1993, 58, 3942.
15. For other methods of synthesizing highly substituted cyclobutenones see. (a) Liebeskind, L. S.; Fengl, R. W ; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482 (b) Gayo, L. M.; Winters, M. P.; Moore, H. W J. Org. Chem. 1992, 57, 6896. (c) Edwards, J. P.; Krysan, D. J.; Liebeskind, L. S. J. Org. Chem. 1993, 58, 3942.
16. Addition of lithium reagents to 2-alkynyl-4-arylcyclobutenones results in ring opening: Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 3274.
17. Butenolide formation has been observed in other cases: (a) Perri, S. T.; Foland, L. D.: Moore, H. W. Tetrahedron Lett. 1988, 29, 3529. (b) Pollart, D. J ; Moore, H. W. J. Org. Chem. 1989, 54, 5444 (c) Moore, H. W.; Perri, S. T. J. Org. Chem. 1988, 53, 996.
18. Butenolide formation has been observed in other cases: (a) Perri, S. T.; Foland, L. D.: Moore, H. W. Tetrahedron Lett. 1988, 29, 3529. (b) Pollart, D. J ; Moore, H. W. J. Org. Chem. 1989, 54, 5444 (c) Moore, H. W.; Perri, S. T. J. Org. Chem. 1988, 53, 996.
19. Butenolide formation has been observed in other cases: (a) Perri, S. T.; Foland, L. D.: Moore, H. W. Tetrahedron Lett. 1988, 29, 3529. (b) Pollart, D. J ; Moore, H. W. J. Org. Chem. 1989, 54, 5444 (c) Moore, H. W.; Perri, S. T. J. Org. Chem. 1988, 53, 996.