A short practical approach to 24R,25-dihydroxyvitamin D3.
A synthesis of the vitamin D3 metabolite 24R,25-dihydroxyvitamin D3 (1) by Lythgoe's Wittig-Horner approach is described. The key step of the synthesis is the stereocontrolled introduction of the 24-hydroxyl group by a palladium(0)-induced [3,3]-sigmatropic rearrangement on a 22R-allylic acetate (7).
Nicoletti
Daniel
D
Departamento de Química Orgánica y Unidad Asociada al C.S.I.C., Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
Gregorio
Carlos
C
Mouriño
Antonio
A
Maestro
Miguel
M
D015650:24,25-Dihydroxyvitamin D 3 / Q000138:chemical synthesis* / Q000737:chemistry; D002117:Calcitriol / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D017102:Fracture Healing; D006801:Humans; D006859:Hydrogen / Q000737:chemistry; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D015650:24,25-Dihydroxyvitamin D 3; D010165:Palladium; D006859:Hydrogen; C021640:calcitroic acid; D002117:Calcitriol