ALTERNATIVE ROUTE TO CARBACYCLIN USING LIPASE-CATALYZED ENANTIOSELECTIVE HYDROLYSIS OF METHYL 8-ACETOXYBICYCLO[4.3.0]NON-3-ENE-7-CARBOXYLATE

Pseudomonas fluorescens lipase was found to catalyse the hydrolysis of the racemic acetate methyl 8-acetoxybicyclo[4.3.0]non-3-ene-7-carboxylate 4 in a highly enantioselective fashion to provide the optically active (-)-methyl 8-hydroxybicyclo[4.3.0]non-3-ene-7-carboxylate (-)-3. This compound was e...

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Published inJournal of the Chemical Society, Perkin Transactions 1 no. 12; pp. 3087 - 3089
Main Authors XIE, ZF, SUEMUNE, H, FUNAKOSHI, K, OISHI, T, AKITA, H, SAKAI, K
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1991
Royal Society of Chemistry
Subjects
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Chemistry
Chemistry, Organic
Enzymes and enzyme inhibitors
Fundamental and applied biological sciences. Psychology
Physical Sciences
Science & Technology
Pseudomonadales
Diol
Catalytic reaction
Vasodilator agent
Enantioselectivity
Enzyme
Enol
Triacylglycerol lipase
Enzymatic catalysis
Pseudomonas fluorescens
Dienic compound
Experimental study
Physical properties
Antiplatelet agent
Hydrolysis
Carboxylic acid
Vinylic compound
Bicyclic compound
Bacteria
Pseudomonadaceae
Chemical properties
NMR spectrum
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Summary:Pseudomonas fluorescens lipase was found to catalyse the hydrolysis of the racemic acetate methyl 8-acetoxybicyclo[4.3.0]non-3-ene-7-carboxylate 4 in a highly enantioselective fashion to provide the optically active (-)-methyl 8-hydroxybicyclo[4.3.0]non-3-ene-7-carboxylate (-)-3. This compound was easily converted into a bicyclo[3.3.0]octane derivative, methyl 3-acetoxy-7-oxobicyclo[3.3.0]octane-2-carboxylate 8, an intermediate in the synthesis of carbacyclin 1.
ISSN:0300-922X
2050-8255
1364-5463
DOI:10.1039/p19910003087