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US 5,254,703 AGranted
Semi-synthesis of taxane derivatives using metal alkoxides and oxazinones
AssigneeFlorida State University
InventorRobert A. Holton
Life of this patent
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Abstract
A process for preparing taxane derivatives taxol by providing a metal alkoxide having the bi, tri-, or tetracyclic taxane nucleus, reacting the metal alkoxide with an oxazinone to form an intermediate, and converting the intermediate to the taxane derivative.
Claims13
A process for the preparation of a taxane derivative comprising:
- providing a metal alkoxide having the tetracyclic taxane nucleus, the metal being a Group IA, IIA, IIIA, IVA, VA, VIA or transition metal and is attached to the oxygen at the C-13 position of the nucleus,
- reacting the metal alkoxide with an oxazinone to form an intermediate, wherein the oxazinone has the formula:
- ##STR25## wherein R.sub.1 is --OR.sub.6 ;
- R.sub.2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl;
- R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or acyl, provided, however, that R.sub.3 and R.sub.4 are not both acyl;
- R.sub.5 is alkyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy or heteroaryloxy;
- and
- R.sup.6 is a hydroxy protecting group;
- and
- converting said intermediate to the taxane derivative by removing the hydroxy protecting group.
7 more elements
A process for the preparation of a taxane derivative comprising:
- providing a metal alkoxide having the tetracyclic taxane nucleus, the metal being a Group IA, IIA, IIIA, IVA, VA, VIA or transition metal and is attached to the oxygen at the C-13 position of the nucleus,
- reacting the metal alkoxide with the oxazinone to form an intermediate, wherein the oxazinone has the formula:
- ##STR28## wherein R.sub.1 is --OR.sub.6 ;
- R.sub.2 is hydrogen;
- R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or acyl, provided, however, that R.sub.3 and R.sub.4 are not both acyl;
- R.sub.5 is alkyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy or heteroaryloxy;
- and
- R.sup.6 is a hydroxy protecting group;
- and
- converting said intermediate to the taxane derivative by removing the hydroxy protecting group.
7 more elements
Dependencies are inferred from the claim text.