Claims
- 1. A process for producing (.+-.)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin, comprising the steps of:
- allowing a carbonate of dihydro-.beta.-vinyl-ionol according to the following formula: ##STR6## wherein R is an alkyl group, to reach with carbon monoxide in the presence of a palladium catalyst to form .beta.-monocyclohomofarnesic acid;
- cyclizing said .beta.-monocyclohomofarnesic acid in the presence of an acid catalyst to form (.+-.)-norambreinolide, according to the following reaction: ##STR7## and hydrolyzing said (.+-.)-norambreinolide to form (.+-.)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin.
- 2. The method according to claim 1, wherein the palladium catalyst is a divalent salt of palladium.
- 3. The method according to claim 1, wherein the palladium catalyst is a catalyst comprising zero valence palladium.
- 4. The method according to claim 1, wherein the palladium catalyst is used in the amount of from 0.001 to 50% by weight based on the carbonate of dihydro-.beta.-vinyl-ionol.
- 5. The method according to claim 4, wherein the palladium catalyst is used in the amount of from 2 to 10% by weight based on the carbonate of dihydro-.beta.-vinyl-ionol.
- 6. The method according to claim 5, wherein the palladium catalyst is used in the amount of from 4 to 6% by weight, based on the carbonate of dihydro-.beta.-vinyl-ionol.
- 7. The method according to claim 1, wherein the palladium catalyst is a supported catalyst.
- 8. The method according to claim 7, wherein the supported catalyst is palladium carbon.
- 9. The method according to claim 8, wherein the palladium carbon is present in the amount of from 3- to 5-fold equivalent weight, based on metallic palladium supported on palladium carbon.
- 10. The method according to claim 1, wherein said carbonate of dihydro-.beta.-vinyl-ionol reacts with carbon monoxide in the presence of a palladium catalyst and a solvent selected from methanol, ethanol, or isopropanol, to form said .beta.-monocyclohomofarnesic acid.
- 11. The method according to claim 10, wherein said solvent is isopropanol.
- 12. The method according to claim 10, wherein said solvent is used in the amount of from about 0.5- to 10-fold by weight based on the carbonate of dihydro-.beta.-vinyl-ionol.
- 13. The method according to claim 10, wherein said solvent is used in the amount of from about 3- to 7-fold by weight based on the carbonate of dihydro-.beta.-vinyl-ionol.
- 14. The method according to claim 1, further comprising introducing carbon monoxide into a reaction vessel at a gas pressure of from 40 to 60 atmospheres, and then allowing said carbonate of dihydro-.beta.-vinyl-ionol according to formula (5) to react with said carbon monoxide in the presence of a palladium catalyst at a reaction temperature of from 40.degree. to 60.degree. C. to form .beta.-monocyclohomofarnesic acid.
- 15. The method according to claim 1, wherein said cyclizing of .beta.-monocyclohomofarnesic acid occurs in the presence of an acid catalyst selected from mineral acids, Lewis acids, or sulfonic acids.
- 16. The method according to claim 15, wherein said acid catalyst is chlorosulfonic acid.
- 17. The method according to claim 1, wherein said cyclizing of .beta.-monocyclohomofarnesic acid occurs in the presence of an acid catalyst and a solvent, said solvent selected from nitroalkanes, chlorinated hydrocarbons, ethers, or acetonitrile.
- 18. The method according to claim 17, wherein said solvent is dichloromethane.
Priority Claims (2)
Number |
Date |
Country |
Kind |
3-358777 |
Dec 1991 |
JPX |
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3-358778 |
Dec 1991 |
JPX |
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Parent Case Info
This is a division, of application Ser. No. 07/995,978, filed on Dec. 23, 1992, now U.S. Pat. No. 5,290,955.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4845272 |
Nohira et al. |
Jul 1989 |
|
4904822 |
Nohira et al. |
Feb 1990 |
|
5066826 |
Nohira et al. |
Nov 1991 |
|
Divisions (1)
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Number |
Date |
Country |
Parent |
995978 |
Dec 1992 |
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