(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Permethric acid

Participants

Reaction Conditions

Reaction Steps

After 100 ml of a liquid medium (pH 6.5, prepared by dissolving 5.0 g of peptone, 10.0 g of glucose, 3.0 g of malt extract and 3.0 g of yeast extract in 1 l of water) was put in a 500 ml flask and sterilized, a loopful of cells of the microorganism each shown in the Table 4 was inoculated from slant culture into the sterilized liquid medium and was subjected to shaking culture at 30° C. for 20 hours. To the cultured solution was added 1.0 g of ethyl (±)-cis, trans-2,2-dimethyl-3(2,2-dichlorovinyl)cyclopropane carboxylate (cis/trans ratio=45/55) and the mixture was reciprocally shaked at 30° C. for 72 hours. Extraction, isolation and analysis of the resulting culture were performed in the same manner as in Example 38 to obtain almost chemically pure 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid (permethric acid). All of the ethyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylate added were recovered as it was excluding that which has been converted to 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid. The analytical results of the reaction performed by each bacterial strain are shown in Table 4. In the table, the yield represents the molar yield of (+)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid to ethyl (+)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylate contained in the starting material.

Provenance & Evidence