Convergent Approaches and Biological Activity of C1 and/or C3 Mono or Diamino Derivatives of 1α,25‐Dihydroxy‐19‐nor‐vitamin D3. Key Enzymatic Desymmetrization of A‐Ring Synthon Precursor

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Abstract
Three novel 19‐nor‐1α,25‐dihydroxyvitamin D3 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

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