Synthesis of fully-substituted enediynes by the corey-winter reaction

Synthetic Communications

Volumn 29, Issue 3, 1999, Pages 359-377

  Crich, D ^a   Pavlovic, A B ^a   Wink, D J ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBONYL DERIVATIVE; 1,6 BIS(TRIMETHYLSILYL) 3,4 BIS(TRIPHENYLMETHOXYMETHYL) 3 HEXEN 1,6 DIYNE; 1,6 DIPHENYL 3,4 BIS(TRIPHENYLMETHOXYMETHYL) 3 HEXEN 1,5 DIYNE; 3,4 BIS(HYDROXYMETHYL) 1,6 DIPHENYL 3 HEXENE 1,5 DIYNE; 4 (TERT BUTYLDIMETHYLSILYLOXY) 4 (TERT BUTYLDIMETHYLSILYLOXYMETHYL) 3 METHYLENE 1,6 DIPHENYL 1,5 HEXYNE; 4 METHYL 1,6 DIPHENYL 3 (TRIPHENYLMETHOXYMETHYL) 3 HEXEN 1,5 DIYNE; ALCOHOL DERIVATIVE; ALKENYLDIALKYNE DERIVATIVE; ALKYNE DERIVATIVE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; PERIODATE SODIUM; RUTHENIUM DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 0032985327     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908085778     Document Type: Article

References (40)

1. Bergman, R., G. Acc. Chem. Res. 1973, 6, 25.
2. Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
3. Shair, M. D.; Yoon, T. Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509.
4. Hitchcock, S. A.; Boyer, S. H.; Chu-Meyer, M. Y.; Olson, S. H.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 858.
5. Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1996, 118, 4904.
6. Nicolaou, K. C.; Hummel, C. W.; Nakada, M.; Shibayama, K.; Pitsinos, E. N.; Saimoto, H.; Mizuno, Y.; Baldenius, K.-U.; Smith, A. L. J. Am. Chem. Soc. 1993, 115, 7625.
7. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimoto, H.; Scarlato, G. R.; suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612.
8. Wisniewski Grissom, J.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603.
9. Tykwinski, R. R.; Diederich, F. Liebigs 1997, 649.
10. Maier, M. M. Synlett. 1995, 13.
11. Lhermitte, H.; Grierson, D. S. Contemorary Organic Synthesis 1996, 3, 41.
12. Lhermitte, H.; Grierson, D. S. Contemporary Organic Synthesis 1996, 3, 93.
13. Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235.
14. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387.
15. Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497.
16. Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866.
17. Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791.
18. Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37.
19. Maier, M. E.; Greiner, B. Liebigs 1992, 855.
20. Bunnage, M. E.; Nicolaou, K. C. Angew 1996, 35, 1110.
21. Bunnage, M. E.; Nicolaou, K. C. Chem Eur J 1997, 3, 187.
22. Anthony, J.; Boldi, A. M.; Rubin, Y.; Hobi, M.; Gramlich, V.; Knobler, C. B.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 13.
23. An isolated example of acetylide addition to a dione, with no assignment of stereochemistry: Birkhofer, L.; Wundram, D. Chem. Ber. 1982, 115, 1132.
24. Corey, E. J.; Winter, R. A. E. J. Am. Chem. Soc. 1963, 85, 2677.
25. Corey, E. J.; Carey, F. A.; Winter, R. A. E. J. Am. Chem. Soc. 1965, 87, 934.
26. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 1979.
27. Block, E. Org. React. 1984, 30, 457.
28. Kocienski, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6.
29. Semmelhack, M. F.; Gallagher, J. Tetrahedron Lett. 1993, 34, 4121.
30. Paquette, L. A.; Itoh, I.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 7280.
31. Green house, R.; Borden, W. T.; Ravindranathan, T.; Hirotsu, K.; Clardy, J. J. Am. Chem. Soc. 1977, 99, 6955.
32. Mitchell, R. H.; Fyles, T.; Ralph, L. M. Can. J. Chem. 1977, 55, 1480.
33. Zibuck, R.; Seebach, D. Helv. Chim. Acta 1988, 71, 237.
34. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828.
35. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic compounds; Wiley: New York, 1994.
36. Crich, D.; Ritchie, T. J. Carbohydr. Res. 1990, 197, 324.
37. Gombler, W. Spectrochim Acta, Part A 1981, 37A, 57.
38. Co-ordinates have been deposited with the Cambridge Crystallographic Database.
39. In XTAL 3.4 User's Manual; Hall, S. R., King, G. S. D., Steward, J. M., Eds.; Lamb: Perth, 1995.
40. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.