A new entry to the stereocontrolled synthesis of CD rings of taxol

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8769-8772

  Yadav, J S ^a   Sasmal, Pradip K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PACLITAXEL;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030834781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10347-1     Document Type: Article

References (26)

1. Taxol is the registered trademark of Bristol-Myers Squibb Company for Paclitaxel.
2. Wani, M.C.; Taylor, H.L.; Wall, M.E.; Coggon, P.; McPhail, A.T. J.Am. Chem. Soc. 1971,93,2325.
3. For a review, see: Nicolaou, K.C.; Dai, W.-M; Guy, R.K. Angew Chem., Int.Ed. Engl. 1994, 33, 15.
4. The total synthesis of Taxol: (a) Nicolaou, K.C.; Yang, Z.; Liu, J.J.; Ueno, H.; Nantermet, P.G.; Guy, R.K.; Claibome, C.F.; Renaud, J.; Couladouros, E.A.; Paulvannan, K.; Sorensen, E.J.Nature. 1994, 367, 630.
5. (b) Holton, R.A.; Kim, H.-B.; Somoza, C.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, J.H. J.Am. Chem. Soc. 1994, 116, 1599.
6. (c) Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem.Int.Ed.Engl. 1995, 34, 1723.
7. (d) Wender, P.A.; Badham, N.F.; Conway, S.P.; Floreancing, P.E.; Glass, T.E.; Houze, J.B.; Krauss, N.E.; Lee, D.; Marquess, D.G.; McGrane, P.L.; Meng, W.; Natchus, M.G.; Shuker, A.J.; Sutton, J.C.; Taylor, R.E. J. Am. Chem.Soc. 1997, 119, 2757.
8. a) Yadav, J.S.; Ravishankar, R. Tetrahedron Lett. 1991, 32, 2629.
9. b) Yadav, J.S. Pure & Appl.Chem. 1993, 65, 1349.
10. c) Yadav, J.S.; Ravishankar, R.; Laxman, S. Tetrahedron Lett. 1994, 35, 3621.
11. d) Yadav, J.S.; Ravishankar, R.; Laxman, S. Tetrahedron Lett. 1994, 35, 3617.
12. e) Yadav, J.S.; Srinivas, D. Tetrahedron Lett. in press.
13. Synthesis of CD rings of Taxol : a) Berkowitz, W.F.; Amarasekara, A.S. Tetrahedron Lett. 1985, 26, 3663.
14. b) Berkowitz, W.F. Amarasekara, A.S. Perumattam, J.J. J. Org. Chem. 1987, 52, 1119.
15. c) Lin, J.; Nikaido, M.M.; Clark, G. J. Org. Chem. 1987, 52, 3745.
16. d) Nicolaou, K.C.; Hwang, C.-K.; Sorenson, E.J.; Clairborne, F. J. Chem. Soc., Chem. Commun. 1992, 1117.
17. e) Magee, T.V.; Bommann, W.G.; Issacs, I.C.A.; Danishefsky, S.J. J. Org. Chem. 1992, 57, 3274.
18. f) Nicolaou, K.C.; Liu, J.J.; Hwang, C.-K.; Dai, W.-M.; Guy, R.K. J. Chem. Soc., Chem. Commun. 1992, 1118.
19. g) Wender, P.A.; Rawlins, D.B. Tetrahedron 1992, 48, 7033.
20. h) Isaacs, R.C.; Di Grandi, M.J.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 3938.
21. i) Sha, C.-K.; Lee, S.-J.; Tseng, W.-H. Tetrahedron Lett. 1997, 38, 2725.
22. Mcbee, E.T.; Crain, D.L.; Crain, R.D.; Belohlav, L.R.; Braendlin, H.P. J.Am. Chem. Soc. 1962, 84, 3557.
23. Feldman, K.S.; Wu, M.-J.; Rotella, D.P. J. Am. Chem. Soc. 1990, 112, 8490.
24. Umbreit, M.A.; Sharpless, K.B. J. Am. Chem. Soc. 1977, 99, 5526.
25. q,J=7.5 Hz, 2H); 4.88-4.70(m,3H); 4.66-4.42(m,6H); 3.78-3.55(m,5H); 3.40(s,3H); 2.68-2.55(m,2H); 2.35-2.02(m,2H).
26. b) IICT communication No. 3891