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 adduct . Vitamin K acid 1 was synthesized in five steps alkylation with a geranyl halide followed by subsequent oxidation reactions, while fully retaining the configuration of the side chain 2',3'-double bond. Vitamin K acid 2 was synthesized in 5 steps from alkylation with dimethylallyl chloride and subsequent oxidation reactions.
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| http://dx.doi.org/10.1055/s-0034-1380002 | DOI Listing |
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