Novel steroidal penta- and hexacyclic compounds derived from 12-oxospirostan sapogenins.
The E ring regioselective acid-catalyzed opening of spirostanic sapogenins possessing a carbonyl group at C-12, such as botogenin and hecogenin, provided the new 12,23-cyclo-22,26-epoxycholesta-11,22-diene skeleton, in addition to new compounds of the already known 12,23-cyclocholest-12(23)-en-22-one frameworks. This transformation proceeds in a single step, under slightly acidic conditions. Both, penta- and hexacyclic steroids were obtained with retention of configuration of all asymmetric centers.
Pérez-Díaz
José Oscar H
JO
Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, México DF, Mexico.
Vega-Baez
José Luis
JL
Sandoval-Ramírez
Jesús
J
Meza-Reyes
Socorro
S
Montiel-Smith
Sara
S
Farfán
Norberto
N
Santillan
Rosa
R
D002384:Catalysis; D012502:Sapogenins / Q000138:chemical synthesis* / Q000737:chemistry*; D013057:Spectrum Analysis; D013141:Spiro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry; D013379:Substrate Specificity
D012502:Sapogenins; D013141:Spiro Compounds; D013256:Steroids; C505698:hecogenin acetate