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Taxol, synthesis

Three different silylene derivatives were used to achieve selective protection of a rnore hindered diol during a taxol synthesis. Treatment of the silylene with MeLi opens the ring to afford the more hindered silyl ether. [Pg.238]

Table 4.21 Summary of reaction metrics and synthesis tree parameters for paclitaxel (taxol) synthesis plans ranked according to overall kernel (maximum) RME. ... Table 4.21 Summary of reaction metrics and synthesis tree parameters for paclitaxel (taxol) synthesis plans ranked according to overall kernel (maximum) RME. ...
Finally, this chapter discusses the synthesis of two taxol components bac-catin III, the polycyclic part of taxol and the side chain of taxol. Although several groups have completed the total synthesis of taxol, work on taxol synthesis is still far from over. Chemists working in the area of asymmetric synthesis will find challenge and opportunity in Section 7.5 of this chapter. [Pg.397]

Another Japanese group developed the Taxol synthesis shown in Scheme 13.47. The eight-membered B ring was closed early in the synthesis using a Lewis acid-induced Mukaiyama reaction (step B-l). Note that a trimethylsilyl dienol ether served as the nucleophile. The C-19 methyl group is introduced via a cyclopropanation in step C-5, followed by a reduction in step D-l. [Pg.887]

Scheme 13.47. Taxol Synthesis H. Kusama, I. Kuwajima, and Co-workers ... Scheme 13.47. Taxol Synthesis H. Kusama, I. Kuwajima, and Co-workers ...
Taxol, synthesis, 265 TEARS see Thiobarbituric acid reactive substances... [Pg.1492]

Wuts and co-workers recently reported that the Vilsmeier reagent is superior to thionyl chloride for the cyclodehydration of primary and secondary p-hydroxy amides to prepare oxazolines, in particular, for oxazoline 18b, which is used in Taxol synthesis (Scheme 8.10). Some other examples are shown in Table 8.5 (Fig. 8.3). As expected, inversion of configuration at the alcohol bearing carbon atom is observed. Of the examples examined, serine afforded low yields due to the formation of dehydroalanine. The reaction is conveniently carried out in pyridine at room temperature. p-Chloro amides are also formed, which can be converted to the oxazoline with DBU, generally using the same mixture without isolation. The... [Pg.347]

The synthesis of this starting material 73 X = SMe also uses interesting strategy. The first step was a Diels-Alder reaction between a cyelopentadiene 77 and the dienophile 62 used by Nicolaou in his taxol synthesis. The diene was made from the anion of cyclopentadiene 74 and ethyl formate,18 and the enolate 76 transformed into the enol acetate 77. Diels-Alder addition of 62 and hydrolysis of the enol ester gave the adduct19 78. [Pg.285]

We shall finish this chapter by returning to Taxol once more. The tricyclic compound drawn here was made in 1996 as an intermediate for Taxol synthesis. The stereochemistry and the conformation of the molecule were deduced by a series of NOE experiments. [Pg.847]

Because of the excellent performance of the new catalysts, many research groups use ringclosing metathesis as the key step in natural product synthesis [12]-[18]. Scheme 6 shows some examples. Via ring-closing metathesis of the olefin 37 to the hydroazulene 38, Blechert et al. [12] succeeded in synthesizing a cyclic system which is part of many sesquiterpenes. Cyclooctane derivatives, whose synthesis is the main problem in taxol synthesis, can be obtained in good yields (39 40), as demonstrated by Grubbs et al. [ 13]. [Pg.93]

Georg, G. I. Harriman, G. C. B. Himes, R. H. MejiUano, M. R. Taxol photoaflinity label 7-(p-azidobenoyl) taxol synthesis and biological evaluation. Bioorg. Med. Chem. Lett., 1993, 2 735-738. [Pg.131]

Intramolecular C-acylation. Treatment of 4-acyl-l,3-dioxan-2-ones such as that appearing as an intermediate for taxol synthesis with LTMP results in ring contraction of the heterocycle. [Pg.226]

Chen S, Farina V, Wei J, Long B, Fairchild C, Mamber SW, Kadow JF, Vyas D, Doyle TW (1994) Structure-Activity Relationships of Taxol Synthesis and Biological Evaluation of C2 Taxol Analogs. Bioorg Med Chem Lett 4 479... [Pg.199]

Georg GI, Harriman GCB (1992) Taxol Photoaffinity Label 7-(p-Azidobenzoyl)-taxol Synthesis and Biological Evaluation. Bioorg Med Chem Lett 2 735... [Pg.202]

Chen S, Combs CM, Hill SE, Farina V, Doyle TW (1992) The Photochemistry of Taxol Synthesis of a Novel Pentacyclic Taxol Isomer. Tetrahedron Lett 33 7679... [Pg.205]

Kant J, Huang S, Wong H, Fairchild C, Vyas D, VF (1993) Studies toward Structure-Activity Relationships of Taxol Synthesis and Cytotoxicity of Taxol Analogues with C-2 Modified Phenylisoserine Side Chains. Bioorg Med Chem Lett 3 2471... [Pg.211]

Scheme 10.1 Palitaxel (Taxol ) synthesis with a Heck coupling as the key step (1). Scheme 10.1 Palitaxel (Taxol ) synthesis with a Heck coupling as the key step (1).
Methods development in the context of taxol synthesis L. Mangatal etal, Tetrahedron 45, 4177 (1989). Synthetic applications S. K. Dubey, E. E. Knaus, Can. J. Chem. 61, 565 (1983) M. Lemaire et al, Synlett 1990, 615. Brief review Organic Syntheses by Oxidation with Metal Compounds, W. J. Mijs, C. R. H. I. de Jonge, Eds. (Plenum Press, New York, 1986) pp 642-645. [Pg.430]


See other pages where Taxol, synthesis is mentioned: [Pg.430]    [Pg.884]    [Pg.886]    [Pg.887]    [Pg.888]    [Pg.889]    [Pg.890]    [Pg.891]    [Pg.125]    [Pg.172]    [Pg.114]    [Pg.296]    [Pg.296]    [Pg.101]    [Pg.884]    [Pg.886]    [Pg.887]    [Pg.888]   
See also in sourсe #XX -- [ Pg.75 ]

See also in sourсe #XX -- [ Pg.208 ]

See also in sourсe #XX -- [ Pg.269 ]

See also in sourсe #XX -- [ Pg.13 , Pg.654 ]

See also in sourсe #XX -- [ Pg.13 , Pg.654 ]




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