Stereoselective synthesis of advanced intermediates en route to Taxuspine U and X: a study of macrocyclization via ring closing metathesis to highly constrained twelve-membered rings

Tetrahedron Letters

Volumn 48, Issue 5, 2007, Pages 751-754

  Galletti, Elena ^a   Avramova, Stanislava I ^a   Renzulli, Michela L ^a   Corelli, Federico ^a   Botta, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

Macrocyclization; Ring closing metathesis; Taxuspine

Indexed keywords

MACROCYCLIC COMPOUND; PACLITAXEL; PLANT EXTRACT; TAXUS CUSPIDATA EXTRACT; TAXUSPINE U; TAXUSPINE X; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 33845871190     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.167     Document Type: Article

References (35)

1. Hosoyama H., Inubushi A., Katsui T., Shigemori H., and Kobayashi J. Tetrahedron 52 (1996) 13145
2. Shigemori H., Wang X.-X., Yoshida N., and Kobayashi J. Chem. Pharm. Bull. 45 (1997) 1205
3. Shigemori H., and Kobayashi J. J. Nat. Prod. 67 (2004) 245-256
4. Manetti F., Maccari L., Corelli F., and Botta M. Curr. Top. Med. Chem. 4 (2004) 203-217
5. Maccari L., Manetti F., Corelli F., and Botta M. Il Farmaco 58 (2003) 659-668
6. Wang M., Xia X.Y., Kim Y., Hwang D., Jansen J.M., Botta M., Liotta D.C., and Snyder J.P. Org. Lett. 1 (1999) 43-46
7. For recent reviews see:. Gradillas A., and Perez-Castells J. Angew. Chem., Int. Ed. 45 (2006) 6086-6101
8. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4490-4527
9. Prunet J. Angew. Chem., Int. Ed. 42 (2003) 2826-2830
10. schrock R.R., and Hoveyda A.H. Angew. Chem., Int. Ed. 42 (2003) 4592-4633
11. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18-29
12. Sanford M.S., Love J.A., and Grubbs R.H. J. Am. Chem. Soc. 123 (2001) 6543-6554
13. Maier M.E. Angew. Chem., Int. Ed. 39 (2000) 2073-2077
14. Furstner A. Angew. Chem., Int. Ed. 39 (2000) 3013-3043
15. Jorgensen M., Hadwiger P., Madsen R., Stutz A.E., and Wrodnigg T.M. Curr. Org. Chem. 4 (2000) 565-588
16. Wright D.L. Curr. Org. Chem. 3 (1999) 211-240
17. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413-4450
18. Armstrong S.K. J. Chem. Soc., Perkin Trans. 1 (1998) 371-388
19. Blechert S., and Schuster M. Angew. Chem., Int. Ed. 36 (1997) 2036-2056
20. Fürstner A., and Langemann K. Synthesis (1997) 792-803
21. Fürstner A., and Langemann K. J. Org. Chem 61 (1996) 3942-3943
22. Renzulli M., Rocheblave L., Avramova S., Corelli F., and Botta M. Tetrahedron Lett. 45 (2004) 5155-5158
23. Renzulli M.L., Rocheblave L., Avramova S.I., Galletti E., Castagnolo D., Tafi A., Corelli F., and Botta M. Tetrahedron 63 (2007) 497-509
24. Job A., Janeck C.F., Bettray W., Peters R., and Enders D. Tetrahedron 58 (2002) 2253
25. Enders D., Voith M., and Iince S.J. Synthesis 12 (2002) 1775
26. 3).
27. 3).
28. Guillame S., Plé K., Banchet A., Liard A., and Haudrechy A. Chem. Rev. 106 (2006) 2355-2403
29. Van de Weghe P., Eustache J., and Cossy J. Curr. Top. Med. Chem. 5 (2005) 1461-1472 and references cited therein
30. Gaich T., and Mulzer J. Curr. Top. Med. Chem. 5 (2005) 1473-1494
31. Van de Weghe P., and Eustache J. Curr. Top. Med. Chem. 5 (2005) 1495-1519
32. 7: C, 68.33; H, 8.21.
33. Schmidt B. Eur. J. Org. Chem. (2004) 1865-1880
34. Hoye T.R., and Zhao H. Org. Lett. 1 (1999) 1123-1125
35. 3).