Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions

Organic Letters

Volumn 4, Issue 6, 2002, Pages 909-912

  Tisdale, Eric J ^a   Chowdhury, Chinmay ^a   Vong, Binh G ^a   Li, Hongmei ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; BIOLOGICAL PRODUCT;

ARTICLE; CHEMISTRY; GARCINIA; OXIDATION REDUCTION REACTION; SYNTHESIS;

ACRYLATES; BIOLOGICAL PRODUCTS; GARCINIA; OXIDATION-REDUCTION;

EID: 0037149677     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017278w     Document Type: Article

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25. Claisen, L. Ber. Dtsch. Chem. Ges. 1912, 45, 3157. For recent and selected reviews on Claisen rearrangement, see: Nowicki, J. Molecules 2000, 5, 1033-1050. Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50. Gajewski, J. J. Acc. Chem. Res. 1997, 30, 219-225. Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452. Wipf, P. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Eds.; 1991; Vol. 5, p 827.
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27. Claisen, L. Ber. Dtsch. Chem. Ges. 1912, 45, 3157. For recent and selected reviews on Claisen rearrangement, see: Nowicki, J. Molecules 2000, 5, 1033-1050. Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50. Gajewski, J. J. Acc. Chem. Res. 1997, 30, 219-225. Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452. Wipf, P. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Eds.; 1991; Vol. 5, p 827.
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32. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
33. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
34. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
35. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
36. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
37. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
38. The tandem Wessely oxidation/Diels-Alder reaction has been utilized extensively by Yates and co-workers. For selected examples on this work, see: Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439-4442. Bhamare, N. K.; Granger, T.; Macas, T. S. Yates, P. J. Chem. Soc., Chem. Comm. 1990, 739-740. Bichan, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773-4774. Yates, P.; Kaldas, M. Can J. Chem. 1992, 70, 2491-2501. Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355. Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun 1976, 1016-1017. Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853-2863.
39. Both the ozonolysis and the Baeyer-Villiger oxidation reactions tended to be clean. This led to the conclusion that hydrolysis of the intermediate formate ester to lactol 26 was the bottleneck of this protocol. Attempts were made to optimize the reaction sequence, particularly the hydrolysis, but little ground could be gained.
40. Wittig olefination of the pendant aldehyde was also attempted prior to hydrolysis of the formate ester. This change in reaction sequence, however, did not change overall product yields.