title: Synthesis of C-19-functionalized 1alpha-hydroxyvitamin D(2) analogues via ring-closing metathesis.
abstract: A heteroatom-tethered regioselective ring-closing metathesis reaction was used for the C-19 functionalization of 1alpha-hydroxy-5,6-trans-vitamin D(2) analogues. Applications of the reaction to form a range of analogues by manipulation of the tether using both organolithium reagents and Diels-Alder cycloadditions are described.
authors.affiliation: Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K.
authors.forename: Mahmood
authors.initials: M
authors.lastname: Ahmed
authors.forename: Catherine E
authors.initials: CE
authors.lastname: Atkinson
authors.forename: Anthony G M
authors.initials: AG
authors.lastname: Barrett
authors.forename: Karine
authors.initials: K
authors.lastname: Malagu
authors.forename: Panayiotis A
authors.initials: PA
authors.lastname: Procopiou
mesh_terms: D003500:Cyclization; D004872:Ergocalciferols / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D008665:Metalloporphyrins / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc
chemical_list: D004872:Ergocalciferols; D007202:Indicators and Reagents; D008665:Metalloporphyrins; C042533:1 alpha-hydroxyergocalciferol; D015032:Zinc