2-(6-carbomethoxy-cis-2-hexenyl)-4(r)-hydroxy-2-cyclopenten-1-one and method for preparing same

Claim 1

A METHOD FOR PREPARING 2-(6-CARBOMETHOXY-CIS-2-HEXENYL)-4(R)-HYDROXY-2-CYCLOPENTEN-1-ONE WHICH COMPRISES: REACTING THE PYRROLIDINE ENAMINE OF ACETO-ACETIC ESTER WITH PROPARGYL BROMIDE SUBJECTING THE RESULTING PRODUCE TO ALKALINE HYDROLYSIS AND DECARBOXYLATION AND RECOVERING 5-OXO-1-HEXYNE REACTING THE 5-OXO-1-HEXYNE WITH ETHYLENE GLYCOL IN THE PRESENCE OF P-TOLUENE SULFONIC ACID TO OBTAIN THE CORRESPONDING CYCLOETHYLENE KETAL, 5-ETHYLNEDIOXY-1-HEXYNE SUBJECTING THE SAID KETAL TO TREATMENT WITH LITHIUM AMIDE IN LIQUID AMMONIA AND TO CONDENSATION WITH 1-BROMO-4TERAHYDROPYRANYLOXYBUTANE IN TETRAHYDROFURAN TO OBTAIN THE EQUIVALENT ETHYLNE KETAL-THP ETHER SUBJECTING THE SAID ETHER TO ACID HYDROLYSIS AND RECOVERING 9-OXO-5-DECYN-1-O1 OXIDIZING THE 9-OXO-5-DECYN-1-O1 WITH JONES REAGENT, ESTERIFYING THE RESULTING PRODUCT UNDER ACID CONDITIONS TO OBTAIN 9-OXO-5-DECYNOIC ACID METHYL ESTER HYDROGENATING THE SAID ESTER OVER LINDLAR''S CATALYST AND RECOVERING 9-OXO-5-CIS-DECEONIC ACID METHYL ESTER CONDENSING THE SAID DECENOIC ACID METHYL ESTER WITH DIETHYL OXALATE, HYDROLYZING THE REACTION PRODUCT UNDER ACID CONDITIONS AND RECOVERING 2-(6-CARBOXY-CIS-5-HEXENYL)CYCLOPENTANE 1,3,4-TRIONE FROM THE RESULTING REACTION MIXTURE REESTERIFYING THE SAID TRIONE, INCUBATING THE RESULTING ESTER, WITH A MICROORGANISM OF THE ORDER ASCOMYCETES AND RECOVERING 2-(6-CARBOMETHOXY-CIS-5-HEXENYL)-4(R)HYDROXY-CYCLOPENTANE-1,3,-DIONE ENOLIZING THE SAID DIONE TO PREFERENTIALLY PROMOTE ACYLATION OR ALKYLATION OF THE OXYGEN AT THE C-1 POSITION AND RECOVERING THE SUBSTITUTED C-1 ENOL REDUCING THE SAID SUBSTITUTED C-1 ENOL WITH A HYDRIDE REDUCING AGENT ACIDIFYING THE REACTION MIXTURE AND RECOVERING 2-(6-CARBOMETHOXY-CIS-2-HENXYL-4(R)-HYDROXY-2CYCLOPENTEN-1-ONE FROM THE REDUCTION REACTION MIXTURE.

Claim 2

A METHOD FOR PREPARING 2-(6-CARBOMETHOXY-CIS-2-HEXENYL)-4(R)-HYDROXY-2-CYCLOPENTEN-1-ONE WHICH COMPRISES: REACTING THE PYRROLIDINE ENAMINE OF ACETO-ACETIC ESTER WITH PROPARGYL BROMIDE SUBJECTING THE RESULTING PRODUCE TO ALKALINE HYDROLYSIS AND DECARBOXYLATION AND RECOVERING 5-OXO-1-HEXYNE REACTING THE 5-OXO-1-HEXYNE WITH ETHYLENE GLYCOL IN THE PRESENCE OF P-TOLUENE SULFONIC ACID TO OBTAIN THE CORRESPONDING CYCLOETHYLENE KETAL, 5-ETHYLNEDIOXY-1-HEXYNE SUBJECTING THE SAID KETAL TO TREATMENT WITH LITHIUM AMIDE IN LIQUID AMMONIA AND TO CONDENSATION WITH 1-BROMO-4TERAHYDROPYRANYLOXYBUTANE IN TETRAHYDROFURAN TO OBTAIN THE EQUIVALENT ETHYLNE KETAL-THP ETHER SUBJECTING THE SAID ETHER TO ACID HYDROLYSIS AND RECOVERING 9-OXO-5-DECYN-1-O1 OXIDIZING THE 9-OXO-5-DECYN-1-O1 WITH JONES REAGENT, ESTERIFYING THE RESULTING PRODUCT UNDER ACID CONDITIONS TO OBTAIN 9-OXO-5-DECYNOIC ACID METHYL ESTER HYDROGENATING THE SAID ESTER OVER LINDLAR''S CATALYST AND RECOVERING 9-OXO-5-CIS-DECEONIC ACID METHYL ESTER CONDENSING THE SAID DECENOIC ACID METHYL ESTER WITH DIETHYL OXALATE, HYDROLYZING THE REACTION PRODUCT UNDER ACID CONDITIONS AND RECOVERING 2-(6-CARBOXY-CIS-5-HEXENYL)CYCLOPENTANE 1,3,4-TRIONE FROM THE RESULTING REACTION MIXTURE REESTERIFYING THE SAID TRIONE, INCUBATING THE RESULTING ESTER, WITH A MICROORGANISM OF THE ORDER ASCOMYCETES AND RECOVERING 2-(6-CARBOMETHOXY-CIS-5-HEXENYL)-4(R)HYDROXY-CYCLOPENTANE-1,3,-DIONE ENOLIZING THE SAID DIONE TO PREFERENTIALLY PROMOTE ACYLATION OR ALKYLATION OF THE OXYGEN AT THE C-1 POSITION AND RECOVERING THE SUBSTITUTED C-1 ENOL REDUCING THE SAID SUBSTITUTED C-1 ENOL WITH A HYDRIDE REDUCING AGENT ACIDIFYING THE REACTION MIXTURE AND RECOVERING 2-(6-CARBOMETHOXY-CIS-2-HENXYL-4(R)-HYDROXY-2CYCLOPENTEN-1-ONE FROM THE REDUCTION REACTION MIXTURE.