Stereospecific keto reduction of bicyclooctandione-carboxylic acid esters by microorganisms

DETAILED DESCRIPTION What is claimed is: 1.
A process for the production of a 3.
alpha.
-hydroxy prostacyclin intermediate product of the formula (+)-I ##STR7## wherein A is the radical >CH--COOR, B is oxygen and R is methyl, comprising treating a racemic bicyclooctanedione of formula (.
+-.
)-II ##STR8## wherein A, B and R have the above-indicated meanings, with a culture of Rhizopus oryzae CBS 32 947 to stereospecifically produce a compound of the formula (+)-I while essentially not altering the compound of the formula (-)-II, and separating the thus-obtained compounds.
2.
A process for the production of a 3.
alpha.
-hydroxy prostacyclin intermediate product of the formula (+)-I ##STR9## wherein A is the radical --CH.
sub.
2 --, B is the double-bond radical --O--X--O-- wherein X is ##STR10## and R is methyl, comprising treating a racemic bicyclooctanedione of formula (.
+-.
)-II ##STR11## wherein A, B and R have the above-indicated meanings, with a culture of Rhodotorula spec.
ATCC 18101 to stereospecifically produce a compound of the formula (-)-I while essentially not altering the compound of the formula (+)-II, and further chemically reducing the unchanged bicyclooctanedione of formula (+)-II after separation from the compound of formula (-)-I.
3.
A process for stereospecifically producing a compound of formula (-)-I ##STR12## wherein A is the radical --CH.
sub.
2 --, B is the double-bond radical --O--X-- wherein X is ##STR13## and R is methyl, comprising treating a racemic bicyclooctanedione of formula (.
+-.
)-II ##STR14## wherein A, B and R have the above-indicated meanings, with a culture of Rhodotorula spec.
ATCC 18101 to stereospecifically produce a compound of the formula (-)-I while essentially not altering the compound of the formula (+)-II, and separating the thus-obtained compounds.




Description:
The invention relates to a microbiological process for stereospecific mono-keto reduction of racemic bicyclic carbacyclin intermediate stages of the formula (.
+-.
)-II to the corresponding optically active 3alpha-hydroxy compounds of the formula (+)-I