title: Synthesis of 1α,25-dihydroxyvitamin D3 analogues with α-hydroxyalkyl substituents at C12.
abstract: Convergent syntheses of three new analogues of 1α,25-dihydroxyvitamin D3 with α-hydroxyalkyl substituents at C12 (4a-c) are described. The A-ring and triene system of each analogue were assembled by a tandem Pd-catalysed intramolecular cyclization and Suzuki-Miyaura coupling process. The stereoselective introduction of substituents at C12 was achieved by Johnson-Claisen rearrangement on allylic alcohol 15 as the key step. This article is part of a Special Issue entitled 'Vitamin D Workshop'.
authors.affiliation: Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
authors.forename: Diego M
authors.initials: DM
authors.lastname: Carballa
authors.forename: Flavia
authors.initials: F
authors.lastname: Zacconi
authors.forename: Urszula
authors.initials: U
authors.lastname: Kulesza
authors.forename: Antonio
authors.initials: A
authors.lastname: Mouriño
authors.forename: Mercedes
authors.initials: M
authors.lastname: Torneiro
mesh_terms: D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002117:Calcitriol