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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Novel steroidal penta- and hexacyclic compounds derived from 12-oxospirostan sapogenins
José Oscar H Pérez-Díaz1, José Luis Vega-Baez, Jesús Sandoval-Ramírez
1Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, México DF, Mexico.
Abstract:
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.
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