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 the same c...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2015-04, Vol.47 (7), p.944-948
Main Authors: Teitelbaum, Aaron M., Scian, Michele, Nelson, Wendel L., Rettie, Allan E.
Format: Article
Language:English
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Summary: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 the same commercially available menadione-cyclopentadiene adduct. Vitamin K acid 1 was synthesized in five steps via alkylation with geranyl bromide followed by subsequent oxidation reactions, while fully retaining the trans -configuration of the side chain 2′,3′-double bond. Vitamin K acid 2 was synthesized in five steps via alkylation with dimethylallyl chloride and subsequent oxidation reactions.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1380002