title: Stereoselective synthesis of 1β,25-Dihydroxyvitamin D3and its 26,27-hexadeuterated derivative.
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.
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
authors.forename: Julian
authors.initials: J
authors.lastname: Loureiro
authors.affiliation: Departamento de Química Fundamental, Universidad de A Coruña, E-15071 A Coruña, Spain.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Maestro
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Mouriño
authors.affiliation: Departamento de Química Orgánica, Laboratorio de Investigación "Ignacio Ribas", Universidade 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
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002117:Calcitriol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D015195:Drug Design; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011485:Protein Binding; D013237:Stereoisomerism; D014807:Vitamin D / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; C118756:dihydroxy-vitamin D3; D014807:Vitamin D; D010165:Palladium; C006923:carvone; D002117:Calcitriol
keywords: 1β,25-Dihydroxyvitamin D(3); Deuterated analogs; Pd-catalyzed cascades; Synthesis; Vitamin D(3) metabolites