Oxidation of cephalomannine with ozone in the presence of taxol

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549200, 435123, 210760, C07D30500, C07D40700, C02F 170

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053347323

ABSTRACT:
A process for oxidizing cephalomannine and related taxanes in the presence of taxol is described. The process involves the use of ozone which is able to oxidize cephalomannine and easily oxidizable taxanes while leaving taxol essentially unchanged. Taxol can then be separated from the oxidized cephalomannine and other oxidized taxanes using conventional procedures. A process for oxidizing taxanes is also provided.

REFERENCES:
Streitweser et al. Intro. to Organic Chemistry, 3d Edition, MacMillan Publishing, New York, pp. 266 & 366.
Kingston et al. Journal of Natural Products, vol. 55(2) pp. 259-261, 1992.
Bunnella, "Preparation, Properties, and Reactions of Carbonyl Oxides", Chem. Rev. 1991, 335-362.
Odinokov et al., "Ozonolysis--A Modern Method in the Chemistry of Olefins", Russian Chemical Reviews, 50 (7), 1981.
Veysoglu et al., "A Convenient Method for the Control of Selective Ozonizations of Olefins", Synthesis, Oct. 1980.
Greenwood et al., "Studies in Ozonolysis. II Quantitatives Study of the Ozonation of 3-Octene", J. Org. Chem. pp. 1551-1554.
Criegee, "Mechanism of Ozonolysis", Chem. Internat. Edit, vol. 14, No. 11 (1975).
Yamamoto et al., "Ozonation of Organic Compounds. 4. Ozonolysis of a,b-unsaturated Carbonyl Compounds in Protic Solvents", J. Org. Chem., 1981, 46, 250-254.
Magri et al., "Modified Taxole. 2. Oxidation Products of Taxol", J. Org. Chem. 1986, 51, 797-802.
Kingston et al., "Modified Taxols. 7. A Method For The Separation of Taxol and Cephalomannine", J. of Natural Products, vol. 55, No. 2, pp. 259-261 (1992).

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