| abstract |
4,5-DISUBSTITUTED-3-HYDROXYCYCLOPENTANONES (I) ARE PREPARED BY HYDROGENOLYZING THE CORRESPONDING 4,5-DISUBSTITUTED-2,3-EPOXYCYCLOPENTANONE (IV) WHICH IN TURN IS PROVIDED BY REACTING THE CORRESPONDING 4,5-DISUBSTITUTED2-CYCLOPENTEN-1-ONE (III) WITH ALKALINE HYDROGEN PEROXIDE. COMPOUNDS III ARE PREPARED BY CYCLIZING THE CORRESPONDING 2,3-DISUBSTITUTED LEVULINALDEHYDE (II) WITH A BASE. THE PRODUCTS OF THE PROCESS ARE BIOLOGICALLY ACTIVE, ESPECIALLY COMPOUND I SUBSTITUTED IN THE 4-POSITION WITH 3''-HYDROXYOCTYL AND IN THE 5-POSITION WITH 6''-CARBOXYHEXYL. THIS COMPOUND HAS PROSTAGLANDIN-LIKE ACTIVITY, ESPECIALLY BLOOD PRESSURE LOWERING AND BRONCHODILATOR ACTIVITY, AND IS A TOTALLY-SYNTHETIC DIHYDROPROSTAGLANDIN E1 (DIHYDRO PGE1). THE PROCESS OF THE INVENTION MAY ALSO BE USED TO OBTAIN COMPOUNDS WITH PROSTAGLANDIN-LIKE ACTIVITY FROM APPROPRIATELY SUBSTITUTED NATURALLY OCCURRING CYCLOPENTANONES, E.G. THOSE ISOLATED FROM THE CARIBBEAN GORGONIAN, PLEXAURA HOMOMALLA. |