Miguel Ferrero

Three novel 19‐ nor ‐1α,25‐dihydroxyvitamin D 3 derivatives modified at C1 and/or C3 with an amino group were synthesized to study the influence of the substitution of one or both hydroxyl groups of A‐ring by amino groups on the affinity for vitamin D receptor (VDR) and vitamin D binding protein (hDBP), and also on the antiproliferative activity. The A‐ring precursors were prepared from cis , cis ‐1,3,5‐cyclohexanetriol applying a desymmetrization reaction of a prochiral 1,3‐diol catalyzed by Pseudomonas cepacia lipase as a key step. The structural elucidation of diastereoisomers were unambiguously assigned by NMR spectroscopy. magnified image