Method of preparing the (+)-isomer of cloprostenol

Details Method of preparing the (+)-isomer of cloprostenol Method of preparing the (+)-isomer of cloprostenol

C - Chemistry, Metallurgy

07

C

260/235.03

C07C 405/00 (2006.01)

Patent

CA 1338188

The (+)-isomer of cloprostenol of formula (I): Image in combination with the (-)-isomer, viz. a racemate, belongs to a significant group of prostaglandin F2 alpha analogues which have found wide use in veterinary medicine. However, only the (+)-isomer of cloprostenol exhibits significant luteolytic effects whereas its (-)-isomer shows just antagonistic effects. The (+)-isomer of cloprostenol may be prepared from an optically active lactone (-)-isomer from which a lactol is obtained by a regio-selective reduction and is then converted by the action of an -ylide to a protected derivative which, after having been deprotected, gives the product of formula (I). In veterinary practice to control livestock oestrus and to induce birth in sows, the (+)-isomer exhibits better tolerance (since only fractions of the usual doses need be administered) which is also very interesting from an economic standpoint.

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