Macrocyclic triarylethylenes via heck endocyclization: A system relevant to diazonamide synthesis

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8640-8641

  Jeong, Susan ^a   Chen, Xin ^a   Harran, Patrick G ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONAMIDE; ETHYLENE DERIVATIVE; LACTAM; TRIARYLETHYLENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0031792110     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981791e     Document Type: Article

References (20)

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4. For other approaches to diazonamide synthesis, see: (a) Wipf, P.; Yokokawa, F, Tetrahedron Lett. 1998, 39, 2223-2226. (b) Jamison, T. F. Ph.D. Thesis, Harvard University, Cambridge, MA, 1997. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997,16, 2413-2419. (d) Vedejs, E.; Wang, J. B. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Society: Washington, DC, 1996; ORGN 93. (e) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Véliz, E. A.; Yang, Z. C. Synlett 1996, 609-611. (f) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107-2110.
5. For other approaches to diazonamide synthesis, see: (a) Wipf, P.; Yokokawa, F, Tetrahedron Lett. 1998, 39, 2223-2226. (b) Jamison, T. F. Ph.D. Thesis, Harvard University, Cambridge, MA, 1997. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997,16, 2413-2419. (d) Vedejs, E.; Wang, J. B. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Society: Washington, DC, 1996; ORGN 93. (e) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Véliz, E. A.; Yang, Z. C. Synlett 1996, 609-611. (f) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107-2110.
6. For other approaches to diazonamide synthesis, see: (a) Wipf, P.; Yokokawa, F, Tetrahedron Lett. 1998, 39, 2223-2226. (b) Jamison, T. F. Ph.D. Thesis, Harvard University, Cambridge, MA, 1997. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997,16, 2413-2419. (d) Vedejs, E.; Wang, J. B. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Society: Washington, DC, 1996; ORGN 93. (e) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Véliz, E. A.; Yang, Z. C. Synlett 1996, 609-611. (f) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107-2110.
7. For other approaches to diazonamide synthesis, see: (a) Wipf, P.; Yokokawa, F, Tetrahedron Lett. 1998, 39, 2223-2226. (b) Jamison, T. F. Ph.D. Thesis, Harvard University, Cambridge, MA, 1997. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997,16, 2413-2419. (d) Vedejs, E.; Wang, J. B. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Society: Washington, DC, 1996; ORGN 93. (e) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Véliz, E. A.; Yang, Z. C. Synlett 1996, 609-611. (f) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107-2110.
8. For other approaches to diazonamide synthesis, see: (a) Wipf, P.; Yokokawa, F, Tetrahedron Lett. 1998, 39, 2223-2226. (b) Jamison, T. F. Ph.D. Thesis, Harvard University, Cambridge, MA, 1997. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997,16, 2413-2419. (d) Vedejs, E.; Wang, J. B. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Society: Washington, DC, 1996; ORGN 93. (e) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Véliz, E. A.; Yang, Z. C. Synlett 1996, 609-611. (f) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107-2110.
9. For other approaches to diazonamide synthesis, see: (a) Wipf, P.; Yokokawa, F, Tetrahedron Lett. 1998, 39, 2223-2226. (b) Jamison, T. F. Ph.D. Thesis, Harvard University, Cambridge, MA, 1997. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997,16, 2413-2419. (d) Vedejs, E.; Wang, J. B. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Society: Washington, DC, 1996; ORGN 93. (e) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Véliz, E. A.; Yang, Z. C. Synlett 1996, 609-611. (f) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107-2110.
10. 4. The product coumarin was reduced to provide a C30 alcohol from which the A-ring oxazole was assembled. Lactamization subsequently closed the 13-membered ring. See ref 2b.
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17. Yields based on analyzing crude HPLC traces and spectroscopic data, retrospectively, after 17a had been fully characterized in latter experiments.
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