Patent ID: 6903225

Claim:
A process for producing a compound of the following general formula (I): wherein R 1 represents hydrogen, an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, R 4 and R 5 each independently represents hydrogen, an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, and R 4 and R 5 may be bound to each other to form a ring, which comprises (1) treating a compound of the following general formula (III): wherein R 2 represents an alkyl group of 1 to 12 carbon atom, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, and X 1 represents a halogen atom, with a Grignard reagent of the following general formula (IX): X 4 —Mg—R 8 (IX) wherein R 8 represents an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, and X 4 represents a halogen atom, in advance and reacting the resulting compound, at a temperature of not less than −30° C., with an enolate prepared by permitting either a base or a metal having a valency of 0 to act on an acetic ester derivative having the following general formula (II): X 2 CH 2 CO 2 R 1 (II) wherein R 1 represents hydrogen, an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, and X 2 represents hydrogen or a halogen atom, to provide a compound of the following general formula (IV): wherein R 1 and X 1 are as defined above; (2) reducing the compound of formula (IV) with the aid of a strain of microorganism to give a compound of the following general formula (V): wherein R 1 and X 1 are as defined above, (3) treating this compound (V) with an acetalizing agent in the presence of an acid catalyst to give a compound of the following general formula (VI): wherein R 1 and X 1 are as defined above, R 4 and R 5 each independently represents hydrogen, an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, and R 4 and R 5 may be bound to each other to form a ring, (4) acyloxylating this compound (VI) with an acyloxylating agent to give a compound of the following general formula (VII): wherein R 1 , R 4 and R 5 are as defined above, R 3 represents hydrogen, an alkyl group of 1 to 12 carbon atoms, an aryl group of 6 to 12 carbon atoms or an aralkyl group of 7 to 12 carbon atoms, and (5) subjecting this compound (VII) to solvolysis in the presence of a base, wherein the strain of microorganism used in the step (2) is selected from among genera of microorganisms belonging to: Homoascus, Candida, Cryptococcus, Debaryomyces, Geotrichum, Kuraishia, Hansenulla, Kluyveromyces, Pichia, Yamadazyma, Rhodotorula, Saccharomyces, Schizoblastosporon, Zygosaccharomyces, Brevibacterium, Corynebacterium, and Rhodococcus.