Stereoselective synthesis of 1β,25-Dihydroxyvitamin D3 and its 26,27-hexadeuterated derivative
Julian Loureiro1, Miguel A Maestro2, Antonio Mouriño1
1Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
Abstract:
A mild convergent synthesis of 1β,25-dihydroxyvitamin D3 (3a), a metabolite of vitamin D3, and its C26,27-hexadeuterated derivative (3b) are described. The A-ring and the CD-fragments are constructed from (R)-carvone and Inhoffen-Lythgoe diol, respectively. The triene system is assembled by a Pd(0)-catalyzed process, which involves an enol-triflate (A-ring fragment) and an alkenyl boronate (CD-side chain fragment). Deuterium labeling is introduced at the last step of the synthesis.
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