Alternative route to carbacyclin using lipase-catalysed enantioselective hydrolysis of methyl 8-acetoxybicyclo[4.3.0]non-3-ene-7-carboxylate
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 23 (12) , 3087-3089
- https://doi.org/10.1039/p19910003087
Abstract
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.Keywords
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