Efficient two-step synthesis of methylphytylbenzoquinones: precursor intermediates in the biosynthesis of vitamin E |
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Authors: | Satyamaheshwar PeddibhotlaZigang Cheng Dean DellaPennaJetze J Tepe |
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Institution: | a Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA b Department of Biochemistry and Molecular Biology Michigan State University, East Lansing, MI 48824, USA |
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Abstract: | Methylphytylbenzoquinone was synthesized from δ-tocopherol by a simple two-step sequence. Oxidative cleavage of the benzopyran ring with cerium sulfate followed by dehydration using Burgess reagent afforded the methylphytylbenzoquinone as a mixture of positional and geometric isomers which were separated by HPLC. The biological activity of the product corresponds to the natural biosynthetic precursor of vitamin E. The above method is a general procedure applicable to the preparation of any of the tocopherol derivatives. |
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