Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol.
A new experimental protocol has been established for the Clemmensen reduction of diosgenin and kryptogenin with the aim to prepare deuterated isotopomers of (25R)-26-hydroxycholesterol. Uncontrolled deuteration has been achieved from diosgenin, whereas [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol (1) can be synthesized from kryptogenin.
Alessandrini
Laura
L
Dipartimento di Scienze Precliniche LITA Vialba, University of Milan, Via G.B. Grassi, 74-20157 Milano, Italy.
Ciuffreda
Pierangela
P
Santaniello
Enzo
E
Terraneo
Giancarlo
G
D003903:Deuterium; D004144:Diosgenin / Q000737:chemistry*; D006865:Hydrogenation; D006888:Hydroxycholesterols / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013261:Sterols / Q000737:chemistry*
D006888:Hydroxycholesterols; D013261:Sterols; C007042:cholest-5-ene-3 beta,26-diol; C008239:kryptogenin; D003903:Deuterium; D004144:Diosgenin