Diastereoselective addition of Grignard reagents to azetidine-2,3-dione: Synthesis of novel Taxol® analogues

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6495-6498

  Kant, Joydeep ^a   Schwartz, Wendy S ^a   Fairchild, Craig ^a   Gao, Qi ^a   Huang, Stella ^a   Long, Byron H ^a   Kadow, John F ^a   Langley, David R ^a   Farina, Vittorio ^a,b   Vyas, Dolatrai ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PACLITAXEL; TAXANE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MICROTUBULE ASSEMBLY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TUMOR CELL;

EID: 16044369708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01420-7     Document Type: Article

References (20)

1. 1. (a) The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: New York, 1995.
2. (b) Suffness, M. In Annual Reports in Medicinal Chemistry: Academic Press, Inc.: San Diego, 1993, 28, 305.
3. (d) Kingston, D.G.I.; Molinero, A.A.; Rimoldi, J.M. Prog. Chem. Org. Nat. Prod. 1993, 61, 1.
4. 2. Wani, M.C.; Taylor, H. L.; Wall, M.E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325.
5. 3. Schiff, P.B.; Fant, J.; Horwitz, S.B. Nature 1979, 277, 665.
6. 4. (a) Kant, J. In The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: New York, 1995; Chapter 6, p 255 and references cited therein.
7. 5. Holton, R.A.; Kim, H-B.; Somoza, C.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1988, 110, 5917.
8. 6. Denis, J-N.; Greene, A.E.; Guénard, D.; Guéritte-Voegelein, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917.
9. 7. (a) Farina, V.; Hauck, S.I.; Walker, D.G. Synlett 1992, 9, 761.
10. (b) Ojima, I.; Habus, I.; Zhao, M.; Georg, G.I.; Jayasinghe, L.R. J. Org. Chem. 1991, 56, 1681.
11. (c) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y.H.; Sun, C.M.; Brigaud, T. Tetrahedron 1992, 48, 6985.
12. 8. Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N. Tetrahedron Lett. 1990, 31, 6429.
13. 3. 3008 refelections (θ = 70°) were measured (ω/2θ) at room temperature on an Enraf-Nonius CAD4 diffractometer with graphic monochromated Cu Kα radiation (λ=1.5418 Å). The structure was solved by direct methods and was refined by full matrix least squares techniques. The final R(F)=0.042 and wR(F)=0.037 for 191 variables and 2240 reflections with unit weights.
14. 10. Kharash, M.S.; Weinhouse, S. J. Org. Chem. 1936, 1, 209; Mosher, H.S.; Mooney, W.T. J. Am. Chem. Soc. 1951, 73, 3948. All new compounds were fully characterized by NMR, HRMS, and CHN analysis.
15. 10. Kharash, M.S.; Weinhouse, S. J. Org. Chem. 1936, 1, 209; Mosher, H.S.; Mooney, W.T. J. Am. Chem. Soc. 1951, 73, 3948. All new compounds were fully characterized by NMR, HRMS, and CHN analysis.
16. 11. Ojima, I. In The Organic Chemistry of β-Lactams; Georg, G.I., Ed.; VCH: New York, 1992; Chapter 5, p 198.
17. 12. Scudiero, D.A.; Shoemaker, R.H.; Paull, K.D.; Monks, A.; Tierney, S.; Nofziger, T.H.; Currens, M.J.; Seniff, D.; Boyd, M.R. Cancer Res. 1988, 48, 4827.
18. 0.01 of paclitaxel.
19. 14. Appendino G. In The Chemistry and Pharmacology of Taxol and its Derivatives; Farina, V., Ed.; Elsevier: New York, 1995; Chapter 2, p 55.
20. 15. Recently, the preparation of 22 and 23 was reported by Greene and co-workers: Denis, J-N.; Fkyerat, A.; Gimbert, Y.; Goutterez, C.; Mantellier, P. Jost, S.; Greene, A.E. J. Chem. Soc., Perkin Trans I. 1995, 1811.