Method for preparation of taxol using an oxazinone

Details Method for preparation of taxol using an oxazinone Method for preparation of taxol using an oxazinone

1989-11-14

1991-05-14

Shen, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549214, 549215, 549332, 549511, 549512, 549513, 549539, 560 27, 560 29, 560 32, 560160, 560162, C07D30500, C07D30300

Patent

active

050157442

ABSTRACT:
Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, ethoxyethyl, 2,2,2-trichloroethoxymethyl or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent under effective conditions to cause the oxazinone to react with the alcohol to form a .beta.-amido ester which is suitable for use as an intermediate in the synthesis of taxol.

REFERENCES:
patent: 4814470 (1989-03-01), Colin et al.
patent: 4857653 (1989-08-01), Colin et al.
patent: 4924011 (1990-05-01), Denis et al.
patent: 4924012 (1990-05-01), Colin et al.
March, Advanced Org. Chem. 3rd Edition, p. 351, Reaction 0-25, Alcoholysis of Esters.
Katritzky, "Handbook of Heterocyclic Chemistry", Pergamon Press, p. 173.
Wani et al., "Plant Antitumor Agents. VI. The Isolation and Structure of Taxol, a Novel Antileukemic and Antitumor Agent from Taxus brevifolia", J. Am. Chem. Soc. 93:9, May 5, 1971, pp. 2325-2327.
Holton, "Synthesis of the Taxane Ring System", J. Am. Chem. Soc., 1984, 106, pp. 5731-5732.
Denis et al., "A Highly Efficient, Practical Approach to Natural Taxol", J. Am. Chem. Soc. 1988, 110, 5917-5919.
Holton et al., "A Synthesis of Taxusin", J. Am. Chem. Soc., 1988, 110, pp. 6558-6560.

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