Taxol chemistry

Mukaiyama, T., Shiina, J., Jwadare, H. et al. (1999) Asymmetric Total Synthesis of Taxol. Chemistry A European Journal, 5, 121-161. 

Two additional reviews on taxol chemistry and biology have been published. One covers its history and gives an overview of its chemistry (572), and the other surveys recent aspects of its chemistry and structure-activity relationships (575). A recent book recounts the history of the development of taxol as a drug, with an emphasis on the difficulties of the supply problem and the controversial agreement with Bristol-Myers Squibb to commercialize it (574). 

Johnson RA, Nidy EG, Dobrowolski PJ, Gebhard I, Qualls SJ, Wicnienski NA, Kelly RC (1994) Taxol Chemistry. 7-O-Triflates as Precursors to Olefins and Cyclopropanes. Tetrahedron Lett 35 7893... 

Chemistry of taxol, anticancer diterpenoid with oxethane cycle as a part of fused system 98PAC331. 

Choudary, B.M., Chowdari, N.S., Mahdi, S., Kantam, M.L. (2003) A Trifimctional Catalyst for One-Pot Synthesis of Chiral Diols via Heck Coupling-N-Oxidation-Asymmetric Dihydroxyla-tion Application for the Synthesis of Diltiazem and Taxol Side Chain. Journal of Organic Chemistry, 6S, 1736-1746. 

Denis, J.N., Corres, A., Greene, A.E. (1991) Direct, Highly Efficient Synthesis from (S)-(-F)-Phenylglycine of the Taxol and Taxotere Side Chains. Journal of Organic Chemistry, 56, 6939-6942. 

Gou, D.M., Liu, Y.C., Chen, C.S. (1993) A Practical Chemoenzymatic Synthesis ofthe Taxol C-13 Side Chain N-Benzoyl-(2R,3S)-3-phenylisoserine. Journal of Organic Chemistry, 58, 1287-1289. 

Feske, B.D., Kaluzna, I.A. and Stewart, J.D. (2005) Enantiodivergent, biocatalytic routes to both taxol side chain antipodes. The Journal of Organic Chemistry, 70 (23), 9654-9657. 

Koepp, A.E., Hezari, M., Zajicek, J. etal. (1995) Cyclization of geranylgeranyl diphosphate to taxa-4(5),l 1(12)-diene is the committed step of Taxol biosynthesis in Pacific yew. Journal of Biological Chemistry, 270, 8686-8690. 

Huang, Q., Roessner, C.A., Croteau, R. and Scott, A.I. (2001) Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of Taxol. Bioorganic Medicinal Chemistry, 9, 2237-2242. 

The structures of taxol and its polycyclic part baccatin III are shown in Figure 7-2, and the numbering of these two compounds is extensively used throughout the rest of this chapter. Because connecting the side chain to baccatin HI is just routine chemistry, we introduce only the synthesis of baccatin III and the taxol side chain. 

Kingston DGl. (1994) Taxol The chemistry and strnctnre-activity relationships of a novel anticancer agent. Trends Biotechnol 12 222-227. 

Guenard D, Gueritte-Voegelein F, Potier P, Taxol andTaxotere Discovery, chemistry and strucmre-activity relationships. Accounts Chem Res 26 160—167, 1993. 

The total synthesis of taxol has only just been accomplished, after nearly two decades of research. The chemistry described (Nicolau et al.,... 

Much of the basis of the BMS CRADA proposal was built on the ability of BMS to tap into the tremendous synthetic knowledge contained in Robert Holton s research group at Florida State University (FSU). This research group had been actively studying the chemistry of Taxol and had made significant strides toward a total synthesis and a viable semi-synthetic pathway from 10-DAB. A licensing agreement between BMS and FSU was created, and in 1992 the first commercially viable semi-synthetic route from 10-DAB to Taxol was discovered [13]. 

Comparison of Semi-Synthetic versus PCF Taxol Green Chemistry Principles... 

Ritter, S.K. (2004) Chem. Eng. News, 82 (27), 4. Also Development of Green Synthesis for Taxol Manufacture via Plant Cell Fermentation and Extraction submitted for 2004 EPA Greener Synthetic Chemistry award, http //www. epa.gov/greenchemistry/pubs/pgcc/ winners/gspa04.html (accessed May 2009). 

A major advantage of the natural products approach to drug discovery is that it is capable of providing complex molecules that would not be accessible by other routes. Compounds such as paclitaxel (Taxol, 8) or rapamycin (10) would never be prepared by standard "medicinal chemistry" approaches to drug discovery, even including the newer methods of combinatorial chemistry. Likewise, the new approach of combinatorial biosynthesis, although an important one, is unlikely in the near future to yield new compounds of the complexity of paclitaxel and camptothecin. 

Volume 22 The Chemistry and Pharmacology of Taxol and its Derivatives edited by l. Farina... 

Gurnard D, Gueritte-Voegelein F and Potier P (1993) Taxol and taxotere discovery, chemistry, and structure-activity relationships. Account Chem Res 26, 160-167. 

Kingston DGI (2000) Recent advances in the chemistry of taxol. J Nat Prod 63, 726-734. 

Wall ME and Wani MC (1998) History and future prospects of camptothecin and taxol. The Alkaloids, Chemistry and Pharmacology (ed Cordell GA) Vol 50. Academic, San Diego, pp 509-536. 

In this chapter, we describe an account of our research on the chemistry and biology of paclitaxel and taxoid anticancer agents (taxoid = taxol-like compound). The topics covered in this chapter include (i) the development of a practical and efficient method for the semisynthesis of paclitaxel and docetaxel using chiral 3-hydroxy-P-lactams as synthetic intermediates, (ii) structure-activity relationship (SAR) studies of various taxoids that led to the discovery of the extremely potent second-generation taxoids, and (iii) biological and conformational studies with the use of fluorine-containing taxoids as probes. ... 

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