title: Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes.
abstract: We report the deacylation of (20R)-20-acetyl-23,24-dinorcholanic lactones by hydrazine hydrate, under microwave irradiation in high yields. The elimination of the 20-acetyl group proceeded with retention of configuration which contrast with other proved deacylation methods that yield a mixture of diastereoisomers. In this way, unnatural (20R)-23,24-dinorcholanic lactones can be produced rapidly on a large scale. Both (20R)- and (20S)-lactones were prepared starting from diosgenin, hecogenin and sarsasapogenin, in 72-80% overall yields.
authors.affiliation: Escuela de Ingeniería Química, Universidad del Istmo, Ciudad Universitaria, Sto. Domingo Tehuantepec, Oaxaca, C.P. 70760, Mexico.
authors.forename: Ma Guadalupe
authors.initials: MG
authors.lastname: Hernández-Linares
authors.forename: Jesús
authors.initials: J
authors.lastname: Sandoval-Ramírez
authors.forename: Socorro
authors.initials: S
authors.lastname: Meza-Reyes
authors.forename: Sara
authors.initials: S
authors.lastname: Montiel-Smith
authors.forename: María A
authors.initials: MA
authors.lastname: Fernández-Herrera
authors.forename: Sylvain
authors.initials: S
authors.lastname: Bernès
mesh_terms: D000215:Acylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D003931:Diacetyl / Q000138:chemical synthesis / Q000737:chemistry*; D004144:Diosgenin / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D012502:Sapogenins / Q000737:chemistry; D013150:Spirostans / Q000737:chemistry; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D000970:Antineoplastic Agents; D006834:Hydrazines; D007783:Lactones; D012502:Sapogenins; D013150:Spirostans; C007908:hecogenin; C046297:sarsasapogenin; D003931:Diacetyl; D004144:Diosgenin