Microbiological Asymmetric Hydroxylation of 7-Carboxybicyclo[2.2.1]heptane and hept-2-ene and Their Methyl Esters Giving Potentially Useful Chiral Synthons for Cyclopentanoids

One hundred and nineteen strains of microorganisms (yeasts, bacteria, actinomycetes and fungi) were screened as to the hydroxylation of bicyclo[2.2.1]heptane-7-carboxylic acid, bicyclo[2.2.1]hept-2-ene-7-syn-carboxylic acid, and their methyl esters. Several species belonging to the genera, Bacillus, Streptomyces, Penicillium, Aspergillus, Absidia, Beauveria, Cunninghamella, Drechslera, Mucor and Chaetomium, were found to asymmetrically hydroxylate some or all of the substrates. Bacillus thuringiensis and Aspergillus awamori were the most effective microorganisms for obtaining the chiral products, (lR)-2-hydroxy acids or esters, with enantiomeric purities of 75~90% e.e., which are potential intermediates for (−)-methyl jasmonate or natural prostaglandins.