Claims
- 1. A chemical compound having the formula: ##STR14## wherein R is an alkyl group and the M.sup.+ counterion is an alkali metal counterion.
- 2. A chemical compound according to claim 1 wherein R is a methyl group.
- 3. A chemical compound according to claim 1 wherein the M.sup.+ counterion is selected from the group consisting of the lithium counterion, potassium counterion and sodium counterion.
- 4. A chemical compound according to claim 1 wherein the M.sup.+ counterion is the lithium counterion.
- 5. A chemical compound according to claim 1 wherein R is a methyl group and M.sup.+ is the lithium counterion.
- 6. A method of producing a compound having a formula: ##STR15## wherein R is an alkyl group and the M.sup.+ counterion is an alkali metal counterion, from a starting compound selected from a group consisting of baccatin III and 10-deacetylbaccatin III comprising the steps of:
- (a) dissolving said starting compound in a first solvent to form a first solution;
- (b) cooling the first solution to a temperature of -20.degree. C. or less;
- (c) thereafter adding to the first solution an alkali base to form an intermediate compound having a metal alkoxide at the C-7 position thereof;
- (d) selectively acylating at the C-10 position any of said intermediate compound present in the first solution where the intermediate compound does not already have an acetyl group at the C-10 position.
- 7. A method of producing a compound according to claim 6 wherein the first solvent is tetrahydrofuran (THF).
- 8. A method of producing a compound according to claim 6 wherein the step of cooling is conducted under a nitrogen atmosphere.
- 9. A method of producing a compound according to claim 6 wherein the starting compound is 10-deacetylbaccatin III and at least two equivalents of the alkali base is added to the first solution.
- 10. A method of producing a compound according to claim 6 wherein the alkali base is selected from the group consisting of n-butyl lithium, potassium hydride and sodium hydride.
- 11. A method of producing a compound according to claim 6 wherein the first solution is stirred for approximately five minutes after adding the alkali base.
- 12. A method of producing a compound according to claim 6 wherein the starting compound is 10-deacetylbaccatin III and the step of selectively acylating is accomplished by adding an acid chloride to the first solution.
- 13. A method of producing a compound according to claim 12 wherein the acid chloride is acetyl chloride.
- 14. A method of producing a compound according to claim 6 wherein the starting compound is 10-deacetylbaccatin III and the step of selectively acylating is accomplished by adding acetic anhydride to the first solution.
- 15. A method of producing a compound according to claim 6 including the additional step of quenching the first solution with a quenching agent.
- 16. A method of producing a compound according to claim 15 wherein the quenching agent is ammonium chloride.
- 17. A method of producing a compound according to claim 6 wherein R is a methyl group and M.sup.+ is Li.sup.+.
RELATED APPLICATIONS
This is a continuation-in-part of application Ser. No. 08/922,684, filed on Sep. 2, 1997, pending, which is a division of application Ser. No. 08/719,488, filed on Sep. 25, 1996, now U.S. Pat. No. 5,750,737, entitled "Method for Paclitaxel Synthesis".
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
5229526 |
Holton et al. |
Jul 1993 |
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5684175 |
Sisti et al. |
Nov 1997 |
|
Non-Patent Literature Citations (1)
Entry |
"A Chemoselective Approach to Functionalize the C-10 Position of 10-Deacetylbaccatin III Synthesis and Biological Properties of Novel C-10 Taxol Analogues", Kant et al, Tetrahedron Letters, vol. 35, No. 31, pp. 5543-5546 (1994). |
Divisions (1)
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Number |
Date |
Country |
Parent |
719488 |
Sep 1996 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
922684 |
Sep 1997 |
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