2′-Methyl taxanes: Synthesis and NMR configurational assignment

Tetrahedron Letters

Volumn 46, Issue 19, 2005, Pages 3411-3415

  Dambruoso, Paolo ^a,b,e   Bassarello, Carla ^b   Bifulco, Giuseppe ^b   Appendino, Giovanni ^a   Battaglia, Arturo ^c   Guerrini, Andrea ^c   Fontana, Gabriele ^d   Gomez Paloma, Luigi ^b  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c CNR   (Italy)

^d INDENA S P A   (Italy)

^e UNIVERSITY OF FERRARA   (Italy)

Author keywords

J Based configurational analysis; Relative configuration; Taxanes; Universal NMR Database

Indexed keywords

METHYL GROUP; TAXANE DERIVATIVE;

ALKYLATION; ARTICLE; DATA BASE; DRUG SYNTHESIS; INFORMATION PROCESSING; INTERMETHOD COMPARISON; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION KINETICS; SOLVATION; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 17144399863     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.095     Document Type: Article

References (27)

1. D.G.I. Kingston, P.G. Jagtap, H. Yuan, and L. Samala Prog. Chem. Org. Nat. Prod. 84 2002 53 225
2. A. Battaglia, R.J. Bernacki, C. Bertucci, E. Bombardelli, S. Cimitan, C. Ferlini, G. Fontana, A. Guerrini, and A. Riva J. Med. Chem. 46 2003 4822 4825
3. J. Kant, W.S. Schwartz, C. Fairchild, Q. Gao, S. Huang, B.H. Long, J.F. Kadow, D.R. Langley, V. Farina, and D. Vyas Tetrahedron Lett. 37 1996 6495 6498
4. J.N. Denis, A. Fkyerat, Y. Gimbert, C. Coutterez, P. Mantellier, S. Jost, and A.E. Greene J. Chem. Soc., Perkin Trans. 1 1995 1811 1815
5. T. Ganesh, R.C. Guza, S. Bane, R. Ravindra, N. Shanker, A.S. Lakdawala, J.P. Snyder, and D.G.I. Kingston Proc. Natl. Acad. Sci. U.S.A. 101 2004 10006 10011
6. I. Ojima, T. Wang, and F. Delaloge Tetrahedron Lett. 39 1998 3663 3666
7. Taxoids bearing norstatin side chains have a better profile of activity against drug-resistant cancer cell lines I. Ojima, J.C. Slater, E. Michaud, S.D. Kuduk, P.Y. Bounaud, P. Vrignaud, M.C. Bissery, J.M. Veith, P. Pera, and R.J. Bernacki J. Med. Chem. 39 1996 3889 3896
8. 3 in refluxing MeOH gave the desired result. Scandium triflate gave lower yields (ca. 70%) compared to DOWEX
9. R.S. Ranganathan, G.H. Jones, and J.G. Moffatt J. Org. Chem. 39 1974 290 298
10. Exposure of 3 to flash chromatography-grade silica gel led to extensive epimerization at C-3′
11. N.F. Magri, and D.G.I. Kingston J. Org. Chem. 51 1986 797 802
12. In sharp contrast to the results observed with Grignard reagents, the use of organolithium species gave complex reaction mixtures that could not be characterized
13. Y. Kobayashi, J. Lee, K. Tezuka, and Y. Kishi Org. Lett. 1 1999 2177 2180
14. J. Lee, Y. Kobayashi, K. Tezuka, and Y. Kishi Org. Lett. 1 1999 2181 2184
15. Y. Kobayashi, C.H. Tan, and Y. Kishi Helv. Chim. Acta 83 2000 2562 2571
16. Y. Kobayashi, C.H. Tan, and Y. Kishi Angew. Chem., Int. Ed. 39 2000 4279 4281
17. C.H. Tan, Y. Kobayashi, and Y. Kishi Angew. Chem., Int. Ed. 39 2000 4282 4284
18. Y. Kobayashi, C.H. Tan, and Y. Kishi J. Am. Chem. Soc. 123 2001 2076 2078
19. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, and K. Tachibana J. Org. Chem. 64 1999 866 876
20. G. Bifulco, C. Bassarello, R. Riccio, and L. Gomez-Paloma Org. Lett. 6 2004 1025 1028
21. R. Roers, and G.L. Verdine Tetrahedron Lett. 42 2001 3563 3565
22. CS ChemNMR Pro version 1.0, Renate Buergin Schaller, Development Center, Bergstrasse 114, Zurich, Switzerland, installed in CS Chem-Draw Pro version 7.0, was used
23. C. Bassarello, G. Bifulco, A. Evidente, R. Riccio, and L. Gomez-Paloma Tetrahedron Lett. 42 2001 8611 8613 and references cited therein
24. A. Battaglia, A. Guerrini, and C. Bertucci J. Org. Chem. 69 2004 9055 9062
25. For a comprehensive review of Seebach's synthetic principle of self-regenerartion of stereocenters ("SRS"), see: D. Seebach, A.R. Sting, and M. Hoffmann Angew. Chem., Int. Ed. Engl. 35 1996 2709 2748
26. For an application of this principle to the synthesis of β-lactams, see: G. Barbaro, A. Battaglia, A. Guerrini, and C. Bertucci J. Org. Chem. 64 1999 4643 4651
27. P. Dambruoso, C. Bassarello, G. Bifulco, G. Appendino, A. Battaglia, G. Fontana, and L. Gomez-Paloma Org. Lett. 7 2005 983 986