title: Efficient Syntheses of Vitamin K Chain-Shortened Acid Metabolites.
abstract: Vitamin K sequentially undergoes ω-oxidation followed by successive rounds of β-oxidation to ultimately produce two chain-shortened carboxylic acid metabolites, vitamin K acid 1 and vitamin K acid 2. Two facile syntheses of these acid metabolites are described, each starting from commercially available menadione-cyclopentadiene adduct3. Vitamin K acid 1 was synthesized in five stepsviaalkylation with a geranyl halide followed by subsequent oxidation reactions, while fully retaining thetransconfiguration of the side chain 2',3'-double bond. Vitamin K acid 2 was synthesized in 5 steps from3viaalkylation with dimethylallyl chloride and subsequent oxidation reactions.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Washington, Seattle, WA 98195.
authors.forename: Aaron M
authors.initials: AM
authors.lastname: Teitelbaum
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Washington, Seattle, WA 98195.
authors.forename: Michele
authors.initials: M
authors.lastname: Scian
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Washington, Seattle, WA 98195.
authors.forename: Wendel L
authors.initials: WL
authors.lastname: Nelson
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Washington, Seattle, WA 98195.
authors.forename: Allan E
authors.initials: AE
authors.lastname: Rettie