Novel synthetic approach to 1alpha,25-dihydroxyvitamin D3 and analogues |
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Authors: | Maestro Miguel Gómez-Reino Clara Nicoletti Daniel Sigüeiro Rita Fraga Ramón Ghini Alberto Torneiro Mercedes Mouriño Antonio |
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Institution: | 1. Departamento de Química Fundamental, Universidad de A Coruña, E-15071 A Coruña, Spain;2. Departamento de Química Orgánica y Unidad Asociada al C.S.I.C., Universidad de Santiago de Compostela, E-15706 Santiago de Compostela, Spain |
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Abstract: | A mild and stereoconvergent synthesis of 1alpha,25-dihydroxyvitamin D(3) (calcitriol, 1a) is described. The key step is a cascade process consisting of two consecutive transformations: An initial palladium-catalyzed 6-exo-cyclocarbopalladation of vinyl triflate 4 followed by a Negishi cross-coupling reaction with alkenyl zinc 3. This approach is of interest for the rapid synthesis of a variety of new vitamin D(3) analogues of therapeutic potential, especially those modified at the triene and ring-A. The mildness of the method also allows the preparation of thermal sensitive vitamin D(3) analogues. |
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