Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes.
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.
Hernández-Linares
Ma Guadalupe
MG
Escuela de Ingeniería Química, Universidad del Istmo, Ciudad Universitaria, Sto. Domingo Tehuantepec, Oaxaca, C.P. 70760, Mexico.
Sandoval-Ramírez
Jesús
J
Meza-Reyes
Socorro
S
Montiel-Smith
Sara
S
Fernández-Herrera
María A
MA
Bernès
Sylvain
S
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
D000970:Antineoplastic Agents; D006834:Hydrazines; D007783:Lactones; D012502:Sapogenins; D013150:Spirostans; C007908:hecogenin; C046297:sarsasapogenin; D003931:Diacetyl; D004144:Diosgenin