Oxazinone compounds for the preparation of taxol
AssigneeFlorida State University
InventorRobert A. Holton
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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, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.
Claims26
An oxazinone of the formula ##STR17## wherein R.sub.1 is aryl, alkyl, alkenyl, alkynyl or --OR.sub.7, R.sub.3, R.sub.5 and R.sub.6 are independently selected from hydrogen alkyl, alkenyl, alkynyl, and aryl, R.sub.7 is alkyl, alkenyl, alkynyl, or aryl, and R.sub.8 is a hydroxyl protecting group.
A process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula ##STR18## wherein R.sub.1 is aryl, alkyl, alkenyl, alkynyl or --OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, or aryl;
- R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, and --OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, or hydroxyl protecting group;
- and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, and aryl, the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent 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.
An oxazinone of the formula ##STR20## wherein R.sub.1 is phenyl or substituted phenyl, alkyl, alkenyl, alkynyl or --OR.sub.7, R.sub.3, R.sub.5 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, phenyl and substituted phenyl, R.sub.7 is alkyl, alkenyl, alkynyl, or phenyl, and R.sub.8 is a hydroxyl protecting group, and the phenyl substituents are selected from alkanoxy, halogen, alkyl, alkenyl, acyl, acyloxy, nitro, amino or amido.
An oxazinone of the formula ##STR21## wherein R.sub.1 is phenyl or substituted phenyl, alkyl, alkenyl, alkynyl or --OR.sub.7, R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, or aryl, R.sub.7 is alkyl, alkenyl, alkynyl, or aryl, R.sub.5 and R.sub.6 are hydrogen, and R.sub.8 is a hydroxyl protecting group and the phenyl substitutents are selected from alkanoxy, halogen, alkyl, alkenyl, acyl, acyloxy, nitro, amino or amido.
An oxazinone of the formula ##STR22## wherein R.sub.1 is aryl, alkyl, alkenyl, alkynyl or --OR.sub.7, R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, or aryl, R.sub.7 is alkyl, R.sub.5 and R.sub.6 are hydrogen, and R.sub.8 is a hydroxyl protecting group.
A process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula ##STR23## wherein R.sub.1 is aryl, alkyl, alkenyl, alkynyl or --OR.sub.7, R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, or aryl, R.sub.7 is alkyl, alkenyl, alkynyl, or aryl, R.sub.5 and R.sub.6 are hydrogen, and R.sub.8 is a hydroxyl protecting group,
- the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent 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.
A process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula ##STR24## wherein R.sub.1 is aryl, alkyl, or --OR.sub.7, R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, or aryl, R.sub.7 is alkyl, alkenyl, alkynyl, or aryl, R.sub.5 and R.sub.6 are hydrogen, and R.sub.8 is a hydroxyl protecting group.
Dependencies are inferred from the claim text.