Production of optically active 4-hydroxycyclopentenones

Abstract

Abstract PURPOSE:To obtain the titled compound useful as an intermediate for agricultural chemicals, perfume, and drugs such as prostaglandin derivatives, etc., by hydrolyzing asymmetrically a specific cyclopentenone ester by the use of an enzyme or a microorganism. CONSTITUTION:1 equivalent dl-4-hydroxycyclopentenone shown by the formula I (R is 1-7C straight-chain alkyl, alkenyl, or alkynyl) is reacted with 1-4 equivalents aliphatic carboxylic acid in the presence(absence) of a solvent by the use of a catalyst at -20-150 deg.C, to give (A) a dl-cyclopentenone ester shown by the formula III (R' is alkyl or alkenyl which may be replaced with halogen). The component A is hydrolyzed with (B) an enzyme such as esterase produced from a microorganism belonging to the genus Pseudomonas, Aspergillus, etc. or a microorganism (e.g., lipase of Aspergillus) in a buffer solution such as 0.05-2M buffer aqueous solution of phosphate, etc., at 10-60 deg.C for 10-70hr with vigorous stirring, to give the titled compound shown by the formula III ( is asymmetric carbon).

Inventors

• 👤 Yuji Ueda
• 👤 裕治 植田
• 👤 Masayoshi Minamii
• 👤 正好 南井

Bibliographic Details