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 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.

Key words

vitamin K acids - C-3 alkylation - 2-methyl-1,4,-naphthoquinone adduct - 5C-aglycones - 7C-aglycones - vitamin K - metabolism

• References

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