title: An efficient convergent synthesis of 1α,25-dihydroxy-3-epi-vitamin D2.
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'.
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain. Electronic address: rita.sigueiro@usc.es.
authors.forename: Rita
authors.initials: R
authors.lastname: Sigüeiro
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
authors.forename: Rocio
authors.initials: R
authors.lastname: Otero
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
authors.forename: Patricia
authors.initials: P
authors.lastname: González-Berdullas
authors.affiliation: Departamento de Química Fundamental, Universidad de A Coruña, E-15071 A Coruña, Spain.
authors.forename: Miguel
authors.initials: M
authors.lastname: Maestro
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Mouriño
mesh_terms: D002117:Calcitriol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D014815:Vitamins / Q000138:chemical synthesis*
chemical_list: D014815:Vitamins; D002117:Calcitriol
keywords: 1α,25-dihydroxy-3-epi-vitamin D(2); Pd-catalyzed cascades; Vitamin D(2) analogues synthesis