Cleavage Of Epoxides Research Articles

Cleavage of steroidal epoxides with organoaluminum cyanides

Cleavage of steroidal epoxides with organoaluminum cyanides

Dimethyl sulphoxide as a solvent for the hydrolytic cleavage of epoxides. Synthesis of the four diastereoisomeric 4-tert-butylcyclohexane-1,2-diols

Dimethyl sulphoxide as a solvent for the hydrolytic cleavage of epoxides. Synthesis of the four diastereoisomeric 4-tert-butylcyclohexane-1,2-diols

Steroid epoxide cleavage by Cylindrocarpon radicicola

When 16α,17α-oxido-pregn-4-ene-3,0-dione (I) was incubated with Cylindrocarpon radicicola four products were obtained. These have been characterized as 20α-hydroxy-16α,17α-oxido-pregn-4-ene-3-one (II), 20α-hydroxy-16α,17α-oxido-pregna-1,4-diene-3-one (III), 16α-hydroxy-17a-oxa-androsta-1,4-diene-3,17-dione (IV) and 16α,17α-dihydroxy-androsta-1,4-diene-3-one (V). When II was exposed to this organism it was readily transformed into III which in turen was converted into IV and V. V was resistant to further attack by this organism. 16α-hydroxy-pregn-4-ene-3,20-dione (XVI) was converted into V by C. radicicola but no IV was detected. The relative rates of metabolism of I and II were found to be similar whereas 16α-hydroxy-androst-4-ene-3,17-dione (XV) was metabolized at a much slower rate into IV and V. A possible mechanism of epoxide opening by C. radicicola has been proposed.

Studies in Steroid Total Synthesis. V. Abnormal Cleavage of Some Tricyclic Ketone Epoxides

Studies in Steroid Total Synthesis. V. Abnormal Cleavage of Some Tricyclic Ketone Epoxides