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US 2007/0166809 A1Published application
Processes for the preparations of optically active cyclopentenones and cyclopentenones prepared therefrom
AssigneeChirogate International Inc.
InventorsYu-Chih Yeh, Ming-Kun Hsu, Shih-Yi Wei
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Abstract
The present invention relates to novel processes for preparing optically active Cyclopentenones of Formula (R)-1, which are useful for the preparation of Prostaglandins and analogs thereof. The invention also relates to novel Cyclopentenones prepared from the processes.
Claims27
A process for preparing an optically active 4-hydroxy-2-cyclopenten-1-one derivative, comprising reacting a racemic mixture of the compound of Formula 1
- wherein R1 is an alkyl, an alkenyl, an alkynyl, an aryl, or an aralkyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, alkyl, aryl, alkoxyl, aryloxy, thioalkoxy, thioaryloxy, alkylamino, arylamino, cyano, alkoxycarbonyl, arylcarbonyl, arylaminocarbonyl, alkylaminocarbonyl, and carbonyl or a heterocyclic group selected from the group consisting of pyridinyl, thiophenyl, furanyl, imidazolyl, morpholinyl, oxazolinyl, piperidinyl, piperazinyl, tetrahydropyranyl, pyrrolidinyl and pyrrolidinonyl, or a protective group for the carboxyl group, with an acyl donor and a lipase derived from Candida antarcitica, Achromobacter spp., Alcaligenese spp., Pseudomonas fluorescens, Pseudomonas stutzri, or Pseudomonas cepacia in the presence of an organic solvent.
A compound of Formula 1A
- wherein X1 is H or a protective group for the hydroxy group;
- and R1 is an alkyl, an alkenyl, an alkynyl, an aryl, or an aralkyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, alkyl, aryl, alkoxyl, aryloxy, thioalkoxyl, thioaryloxy, alkylamino, arylamino, cyano, alkoxycarbonyl, arylcarbonyl, arylaminocarbonyl, alkylaminocarbonyl, and carbonyl or a heterocyclic group selected from the group consisting of pyridinyl, thiophenyl, furanyl, imidazolyl, morpholinyl, oxazolinyl, piperidinyl, piperazinyl, tetrahydropyranyl, pyrrolidinyl and pyrrolidinonyl, or a protective group for the carboxyl group, with the proviso that R1 is not a straight, unsubstituted alkyl.
Dependencies are inferred from the claim text.