Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4651-4654

  Ghosh, Arun K ^a   Cappiello, John ^a   Shin, Dongwoo ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ALKENE; DELTA LACTONE; HYDROXYETHYLENE; LACTONE; TITANIUM ISOPROPOXIDE; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; HUMAN IMMUNODEFICIENCY VIRUS; METAL BINDING; NONHUMAN; PROTEINASE INHIBITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032566021     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00887-9     Document Type: Article

References (27)

1. 1. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc.Chem.Res. 1995, 28, 446;
2. (b) Schuster, M.; Blechert, S. Angew. Chern. Int. Ed. Engl. 1997, 36, 2036 and references cited therein.
3. 2. (a) Fu, G. C.; Nguyen, S. B. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9858;
4. (b) Fu, G. C.; Grubbs, R.H. J. Am. Chem. Soc. 1992, 114, 7324;
5. (c) Fu, G. C.; Nguyen, S. B. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856 and references cited therein.
6. 3. For recent applications in the synthesis of macrocycles: (a) Yang, Y.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2801;
7. (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Nikovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Glannakakou, P.; Hamel, E. Nature 1997, 387, 268;
8. (c) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 117, 10073;
9. (d) Su, D.-S.; Meng, D.; Bertinato, P.; Balog, A.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C; He, L.; Horwitz, S. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 757;
10. (e) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302;
11. (f) Balog, A.; Meng, D.; Kamenecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1996, 35, 2801;
12. (g) Fürstner, A.; Langermann, K. J. Org. Chem. 1996, 61, 3942;
13. (h) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943 and references cited therein.
14. 4. For the synthesis of medium size rings, see: (a) Linderman, R. J.; Siedlecki, J.; O'Neill, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919;
15. (b) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548;
16. (c) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291;
17. (d) Fu, G. C.; Nguyen, S. T. Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856 and references cited therein.
18. 5. Ghosh, A. K. ; Hussain, K. A.; Tetrahedron Lett. 1998, 39, 1881.
19. 6. Fürstner, A.; Langermann, K. J. Am. Chem. Soc. 1997, 119, 9130.
20. 7. (a) Ghosh, A. K.; McKee, S. P.; Thompson, W. J.; Darke, P. L.; Zugay, J. C. J. Org. Chem. 1993, 58, 1025;
21. (b) Ghosh, A. K.; Thompson, W. J.; McKee, S. P.; Duong, T. T.; Lyle, T. A.; Cen, J. C.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1993, 36, 292;
22. (c) Ashorn, P.; McQuade, T. J.; Thaisrivongs, S.; Tomasselli, A. G.; Tarply, W. G.; and Moss, B.; Proc. Natl. Acad. Sci. USA. 1990, 87, 7472 and references cited therein.
23. 8. Danishefsky, S. J.; DeNinno, M. P.; Phillips, G. B.; Zelle, R. E.; Cartey, P. A. Tetrahedron 1986, 42, 2809.
24. 9. Thompson, W. J.; Tucker, T. J.; Schwering, J. E.; Barnes, J. L. Tetrahedron Lett. 1990, 31, 6819.
25. 10. Vara Prasad, J. V. N.; Rich, D. H. Tetrahedron Lett. 1990, 31, 1803.
26. 11. All new compounds gave satisfactory spectroscopic and analytical results.
27. 12. Basha, A.; Lipton, M.; and Weinreb, S. M.; Tetrahedron Lett. 1977, 4171.