Efficient two-step synthesis of methylphytylbenzoquinones: Precursor intermediates in the biosynthesis of vitamin E

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 237-239

  Peddibhotla, Satyamaheshwar ^a   Cheng, Zigang ^b   DellaPenna, Dean ^b   Tepe, Jetze J ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 6 PHYTYL 1,4 BENZOQUINONE; ALPHA TOCOPHEROL; BENZOPYRAN DERIVATIVE; BENZOQUINONE DERIVATIVE; CERIUM; METHYLTRANSFERASE; REAGENT; SULFATE; UNCLASSIFIED DRUG;

ARTICLE; DEHYDRATION; DRUG ACTIVITY; DRUG SYNTHESIS; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PRECURSOR; THIN LAYER CHROMATOGRAPHY;

EID: 18744382120     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02564-9     Document Type: Article

References (19)

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18. Procedure for the dehydration of methylphytyl benzoquinol 1: The quinone alcohol 1 (0.4 g, 9 mmol) was weighed into a flame dried flask under argon atmosphere and dry THF (50 mL) was added. To this solution was added Burgess reagent (0.4 g, 1.8 mmol) and the mixture stirred at room temperature overnight. The reaction mixture was then diluted with ether (200 mL) and extracted twice with water and the organic layer was dried over anhydrous sodium sulfate and the ether layer was evaporated to obtain a yellow residue. The residue was flash chromatographed on silica-gel (5% ether:hexane) to obtain the methylphytylbenzoquinone as a mixture of five isomers (0.16 g, 42%) They were further separated by HPLC.
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