Beckmann reactions of steroidal spirocyclic oximes derived from the 16beta,23:23,26-diepoxy-22-oxo moiety.
The Beckmann rearrangement of the syn and anti isomers of the spirocyclic oxime derived from a 16beta,23:23,26-diepoxy-5beta-cholestan-22-one was studied. Whereas the anti isomer always follows the Beckmann fragmentation course, the syn isomer, depending on the reaction conditions, follows the normal Beckmann rearrangement course and/or the isomerization to the anti isomer followed by the fragmentation course.
Macías-Alonso
Mariana
M
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México D.F., Mexico.
Flores-Alamo
Marcos
M
Iglesias-Arteaga
Martín A
MA
D002778:Cholestanones / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D012502:Sapogenins / Q000138:chemical synthesis* / Q000737:chemistry
D002778:Cholestanones; D010091:Oximes; D012502:Sapogenins