Synthesis of cholaphanes by ring closing metathesis

Tetrahedron Letters

Volumn 48, Issue 16, 2007, Pages 2851-2855

  Czajkowska, Dorota ^a   Morzycki, Jacek W ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CHOLAPHANE DERIVATIVE; CHOLIC ACID DERIVATIVE; MACROCYCLIC COMPOUND; PHTHALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; RING CLOSING METATHESIS; SYNTHESIS;

EID: 33947221944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.099     Document Type: Article

References (28)

1. Davis A.P. Chem. Soc. Rev. (1993) 243-253
2. Li Y., and Dias J.R. Chem. Rev. 97 (1997) 283-304
3. Wallimann P., Marti T., Furer A., and Diederich F. Chem. Rev. 97 (1997) 1567-1608
4. Tamminen J., and Kolehmainen E. Molecules 6 (2001) 21-46
5. Davis A.P., and Joos J.B. Coord. Chem. Rev. 240 (2003) 143-156
6. Bonar-Law R.P., and Davis A.P. Tetrahedron 43 (1993) 9829-9844
7. Bonar-Law R.P., and Davis A.P. Tetrahedron 43 (1993) 9845-9854
8. Bonar-Law R.P., Davis A.P., and Dorgan B.J. Tetrahedron 43 (1993) 9855-9866
9. Virtanen E., and Kolehmainen E. Eur. J. Org. Chem. 16 (2004) 3385-3399
10. Łotowski Z., and Guzmański D. Monatsh. Chem. 137 (2006) 117-124
11. Li Y., and Dias J.R. Synthesis (1997) 425-430
12. Lappalainen K., and Kolehmainen E. Liebigs Ann. Recl. (1997) 1965-1968
13. Brady P.A., and Sanders J.K.M. J. Chem. Soc., Perkin Trans. 1 (1997) 3237-3253
14. Pandey P.S., Rai R., and Singh R.B. J. Chem. Soc., Perkin Trans. 1 (2002) 918-923
15. Virtanen E., Koivukorpi J., Tamminen J., Mänttäri P., and Kolehmainen E. J. Organomet. Chem. 668 (2003) 43-50
16. Ghosh S., Choudhury A.R., Row T.N.G., and Maitra U. Org. Lett. 7 (2005) 1441-1444
17. Davis A.P., Gilmer J.F., and Perry J.J. Angew. Chem., Int. Ed. 35 (1996) 1312-1315
18. Bhattarai K.M., Davis A.P., Perry J.J., and Walter C.J. J. Org. Chem. 62 (1997) 8463-8473
19. Albert D., and Feigel M. Helv. Chim. Acta 80 (1997) 2168-2181
20. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
21. Connon S.J., and Blechert S. Angew. Chem., Int. Ed. 42 (2003) 1900-1923
22. Fürstner A. Angew. Chem., Int. Ed. 39 (2000) 3012-3043
23. Schmidt B. Eur. J. Org. Chem. (2004) 1865-1880
24. General procedure for the ring-closing metathesis reaction: To a solution of a Grubbs' catalyst (0.002 mM, 25 mol %) in dry toluene (10 mL), a solution of dimer (0.008 mM) in dry toluene or dichloromethane (10 mL) was added dropwise (over 30 min). The resulting mixture was stirred at 30 °C for 1 h under argon.
25. Morsman H., Steiger M., and Reichstein T. Helv. Chim. Acta 20 (1937) 3-16
26. Hoehn W.M., and Mason H.L. J. Am. Chem. Soc. 60 (1938) 1493-1497
27. Carlson G.L., Belobaba D.T.E., and Hofmann A.F. Steroids 30 (1977) 787-793
28. Davis A.P., and Walsh J.J. J. Chem. Soc., Chem. Commun. (1996) 449-451