Synthesis of novel thiol taxoids based on the 7,10-di-(2,2,2- trichloroethyloxycarbonyl)-10-deacetylbaccatin III: Both the syn and anti 10-deacetyl-2′-deoxy-2′-mercaptopaclitaxels

Tetrahedron

Volumn 60, Issue 19, 2004, Pages 4133-4138

  Qi, Xin ^a,b   Lee, Sang Hyeup ^b   Yoon, Juyoung ^c   Lee, Yoon Sik ^b  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b Seoul National University   (South Korea)

^c Ewha Womans University   (South Korea)

Author keywords

Mercapto taxoid; Oxazoline; Taxol

Indexed keywords

BACCATIN III; OXAZOLINE DERIVATIVE; PACLITAXEL DERIVATIVE; TAXOID; THIOACETIC ACID; THIOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; DRUG SYNTHESIS; EPIMERIZATION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

EID: 1942471997     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.03.064     Document Type: Article

References (26)

1. Wani M.C., Taylor H.L., Wall M.E., Coggon P., McPhail A.T. J. Am. Chem. Soc. 93:1971;2325.
2. Baloglu E., Kingston D.G.I. J. Nat. Prod. 62:1999;1448.
3. For a review on clinical utility, see: (a) Rowinsky E.K. Annu. Rev. Med. 48:1997;353.
4. Herz W., Falk H., Kirby G.W. Progress in the chemistry of organic natural products. 2002;53 Springer, Wien, Austria.
5. Baloglu E., Hoch J.M., Chatterjee S.K., Ravindra R., Bane S., Kingston D.G.I. Bioorg. Med. Chem. 11:2003;1557.
6. Lozyński M., Rusińska-Roszak D. Tetrahedron Lett. 36:1995;8849.
7. Jiménez-Barbero J., Souto A.A., Abal M., Barasoain I., Evangelio J.A., Acuña A.U., Andreu J.M., Amat-Guerri F. Bioorg. Med. Chem. 6:1998;1857.
8. Kant J., Huang S., Wong H., Fairchild C., Vyas D., Farina V. Bioorg. Med. Chem. Lett. 3:1993;2471.
9. Guénard D., Guéritte-Voegelein F., Potier P. Acc. Chem. Res. 26:1993;160.
10. Moyna G., Williams H.J., Scott A.I. Synth. Commun. 27:1997;1561.
11. Qi X., Lee S.-H., Yoon J., Lee Y.-S. Tetrahedron. 59:2003;7409.
12. Qi X., Lee S.-H., Yoon J., Lee Y.-S. Tetrahedron. 60:2004;3599.
13. Ojima I., Sun C.M., Zucco M., Park Y.H., Duclos O., Kuduk S. Tetrahedron Lett. 34:1993;4149.
14. Ojima I., Habus I., Zhao M.Z., Zucco M., Park Y.H., Sun C.M., Brigaud T. Tetrahedron. 48:1992;6985.
15. Wahl A., Guéritte-Voegelein F., Guénard D., Le Goff M.-T., Potier P. Tetrahedron. 48:1992;6965.
16. Commercon A., Bézard D., Bernard F., Bourzat J.D. Tetrahedron Lett. 33:1992;5185.
17. Mangatal L., Adeline M.-T., Guénard D., Guéritte-Voegelein F., Potier P. Tetrahedron. 45:1989;4177.
18. Guéritte-Voegelein F., Sénilh V., David B., Guénard D., Potier P. Tetrahedron. 42:1986;4451.
19. Jagtap P.G., Baloglu E., Barron D.M., Bane S., Kingston D.G.I. J. Nat. Prod. 65:2002;1136.
20. Chordia M.D., Yuan H., Jagtap P.G., Kadow J.F., Long B.H., Fairchild C.R., Johnston K.A., Kingston D.G.I. Bioorg. Med. Chem. 9:2001;171.
21. Ojima I., Lin S., Slater J.C., Wang T., Pera P., Bernacki R.J., Ferlini C., Scambia G. Bioorg. Med. Chem. 8:2000;1619.
22. Bhat L., Liu Y., Victory S.F., Himes R.H., Georg G.I. Bioorg. Med. Chem. Lett. 8:1998;3181.
23. Liu Y., Ali S.M., Boge T.C., Georg G.I., Victory S., Zygmunt J., Marquez R.T., Himes R.H. Comb. Chem. High Throughput Screen. 5:2002;39.
24. Xiao X.-Y., Parandoosh Z., Nova M.P. J. Org. Chem. 62:1997;6029.
25. Lee S.-H., Qi X., Yoon J., Nakamura K., Lee Y.-S. Tetrahedron. 58:2002;2777.
26. Lee S.-H., Yoon J., Nakamura K., Lee Y.-S. Org. Lett. 2:2000;1243.