title: Synthesis of spiro[4.5]decane CF-ring analogues of 1 alpha,25-dihydroxyvitamin D3.
abstract: A novel series of analogues of calcitriol (1) is developed featuring a spirocyclic central core resulting from C18/C21-connection and C15/C16-deletion (2a, 2b). The synthesis of the key intermediate involves an Eschenmoser rearrangement of an enantiomerically pure bromo-substituted cyclohexenol.
authors.affiliation: Department of Organic Chemistry, Ghent University, Krijgslaan 281, B-9000 Gent, Belgium.
authors.forename: Wim
authors.initials: W
authors.lastname: Schepens
authors.forename: Dirk
authors.initials: D
authors.lastname: Van Haver
authors.forename: Maurits
authors.initials: M
authors.lastname: Vandewalle
authors.forename: Roger
authors.initials: R
authors.lastname: Bouillon
authors.forename: Annemieke
authors.initials: A
authors.lastname: Verstuyf
authors.forename: Pierre J
authors.initials: PJ
authors.lastname: De Clercq
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002117:Calcitriol / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D002117:Calcitriol; C012867:decane