Intermediates for the synthesis of benzindene prostaglandins and preparations thereof
Novel processes for preparing optically active cyclopentanones 1 which are useful for the preparation of benzindene Prostaglandins and novel cyclopentanones are provided. The invention also provides novel processes of preparing benzindene Prostaglandins and novel intermediates for benzindene Prostaglandins.
1. A process for preparing the compound of Formula 8d
comprising the steps of:
(1) esterifying the compound of Formula 6d
wherein P 2 and P 3 are protecting groups for the hydroxyl groups, to form an ester compound of Formula 10d
wherein M is a lower alkyl, or an unsubstituted or substituted phenyl;
(2) removing the P 2 and P 3 groups to form a compound of Formula 11d
(3) hydrogenating the double bond in the ω-side chain of the compound of Formula 11d and then deacylating the hydrogenated compound; or deacylating the compound of Formula 11d and then hydrogenating the double bond in the ω-side chain of the deacylated compound to form a compound of Formula 8d.
2. The process according to claim 1 , wherein M is phenyl or 4-phenylphenyl.
3. A compound of Formula 1e
wherein P 1 is an unsubstituted or substituted benzyl; is single bond or double bond; R 2 is a single bond or a C 1-4 -alkylene or —CH 2 O—; R 3 is a C 1-7 -alkyl or an aryl or an aralkyl group, each of which is unsubstituted or substituted by a C 1-4 -alkyl, a halogen, or a trihalomethyl; P 2 ′ and P 3 ′ are respectively P 2 and P 3 as defined in claim 1 as protecting groups for the hydroxy group or are independently H.
4. A compound of Formula 8D-1
5. A compound of Formula 11-1
wherein M is methyl, phenyl or 4-phenylphenyl; and is a single or double bond.