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Published on: December 9, 2015
An efficient convergent synthesis of 1α,25-dihydroxy-3-epi-vitamin D2
Rita Sigüeiro1, Rocio Otero1, Patricia González-Berdullas1
1Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
Abstract:
The first synthesis of 1α,25-dihydroxy-3-epi-vitamin D2 is described. Key steps of the synthesis entail the construction of the triene unit by a Pd-catalyzed ring closure of an enol-triflate (A-ring fragment) followed by a Suzuki-Miyaura coupling with a boronate (upper fragment), and the installation of the methyl group at C-24 by an SN2'-syn displacement of an allylic carbamate. This article is part of a Special Issue entitled 'SI:17th Vitamin D Workshop'.
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