Acid catalyzed rearrangement and acyl migration studies on 9-dihydro- 13-acetylbaccatin-III, a major taxane from Taxus canadensis

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 15991-16008

  Zamir, Lolita O ^a   Balachandran, Sarala ^a   Zheng, Yi Feng ^a   Nedea, Maria E ^a   Caron, Gaétan ^a   Nikolakakis, Anastasia ^a   Vishwakarma, Ram A ^b   Sauriol, Françoise ^c   Mamer, Orval ^c  

^a UNIVERSITÉ LAVAL   (Canada)

^b NATIONAL INSTITUTE OF IMMUNOLOGY   (India)

^c MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

9 DIHYDRO 13 ACETYLBACCATIN III; PLANT EXTRACT; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DEACYLATION; DRUG CONFORMATION; DRUG ISOLATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

TAXUS CANADENSIS;

EID: 0030698782     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10069-2     Document Type: Article

References (21)

1. Witherup, K. M.; Look, S.A.; Stasko, M. W.; Ghiorzi, T. J.; Muschik, G. M.; Cragg, G. M. J. Nat. Prod. 1990, 53, 1249-1255
2. Zamir, L. O.; Nedea, M. E.; Garneau, F.-X. Tetrahedron Lett., 1992, 33, 5235-5236
3. Zamir, L. O.; Nedea, M. E.; Bélair, S.; Sauriol, F.; Mamer, O.; Jacqmain, E.; Jean F. I; Garneau, F.-X. Tetrahedron Lett., 1992, 33, 5173-5176
4. Zamir, L. O.; Nedea, M. E.; Zhou, Z. H.; Bélair, S.; Caron, G.; Sauriol, F.; Jacqmain, E.; Jean, F. I.; Garneau, F.-X.; Mamer, O. Can. J. Chem. 1995, 73, 655-665
5. Zamir, L. O.; Nedea, M. E.; Zhou, Z. H.; Caron, G.; Sauriol, F.; Mamer O. Phytochemistry. 1996, 41, 803-805
6. Gunawardana, G. P.; Premachandran, U.; Burres, N. S.; Whittern, D. N.; Henry, R.; Spanton, S.; McAlpine, J. B. J. Nat. Prod. 1992, 55, 1686-1689
7. Zamir, L. O.; Zhou Z. H.; Caron, G.; Nedea, M. E.; Sauriol, F.; Mamer O. J. Chem. Soc., Chem. Commun., 1995, 529-530
8. Boulanger, Y.; Khiat, A.; Zhou Z, H.; Caron, G.; Zamir, L.O. Tetrahedron, 1996, 52, 8957-8968
9. (a) Appendino, G.; Ozen, H. C.; Gariboldi, P.; Torregiani, E.; Gabetta, B.; Nizzola, R.; Bombardelli, E. J. Chem. Soc., Perkin. Trans. 1. 1993, 1563-1566
10. (b) Fuji, K.; Tanaka, K.; Li, B.; Shingu, T.; Yokoi, T.; Sun, H. D.; Taga, T. Tetrahedron, 1995, 51, 10175-10188 and references cited therein.
11. (c) Blaza, F.; Tachibana, S.; Barrios, H.; Towers, G. N. H. Phytochemistry, 1991, 30, 1613-1614.
12. (d) Using Lewis acids in aprotic solvent does not favor A-ring rearrangement. Chen, S-H.; Huang, S.; Wei, J.; Farina, V. Tetrahedron, 1993, 49, 2805-2828
13. (e) A-Ring rearrangements were observed in the presence of DAST. Chen, S.-H.; Huang, S.; Wei, J.; Farina, V. J. Org. Chem., 1993, 58, 4520-4545.
14. (f) Chen, S.-H.; Huang, S.; Farina, V. Tetrahedron Lett., 1994, 35, 41-44
15. Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Kirby, G. W.; Moore, R. E.; Tamm, C. Ed.; Springer-Verlag, New York, 1993, 61, pp. 1-188.
16. Zamir, L. O.; Zheng, Y. F.; Caron, G.; Sauriol, F.; Mamer, O. Tetrahedron Lett., 1996, 37, 6435-6438
17. Vander Velde, D. G.; Georg, G.I.; Gollapudi, S. R.; Jampani, H. B.; Liang, X.-Z.; Mitscher, L. A.; Ye, Q.-M. J. Nat. Prod. 1994, 57, 862-867
18. Zhang, S.; Chen, W. M.; Chen, Y. H. Yaoxue Xuebao, 1992, 27, 268-270
19. Klein, L. L. Tetrahedron Lett. 1993, 34, 2047-2050
20. Chu, A.; Davin, L. B.; Zajicek, J.; Lewis, N. G.; Croteau, R. Phytochemistry, 1993, 34, 473-476
21. Klein, L. L.; Li, L.; Maring, C. J.; Yeung, C. M.; Thomas, S. A.; Grampovnik, D. J.; Plattner, J. J. J. Med. Chem. 1995, 38, 1482-1492