Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 6, Issue 6, Pages 782-787Publisher
AMER CHEMICAL SOC
DOI: 10.1021/op020216g
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The use of the biologically derived diterpene alcohol geranylgeraniol was explored as an alternative to petrochemical-based isophytol as a side-chain synthon for producing D,L-alpha-tocopherol. Two routes were studied, both of which begin with allylic epoxidation followed by olefin hydrogenation to give epoxyphytol. Epoxyphytol can be reduced with Red-Al to provide phytan-1,3-diol which upon acid-catalyzed condensation with trimethylhydroquinone gives vitamin E in fair yield. In a higher-yielding process, epoxyphytol was deoxygenated with methylrhenium,trioxide/triphenylphosphine to generate a mixture of phytol and isophytol (>90% yield from geranylgeraniol). This mixture can serve as a plug-in replacement for isophytol in the final step of the currently practiced vitamin E chemistry. The use of methylrhenium trioxide to catalyse dehydration of vinyl dialkyl carbinols to 1,3-dienes was also demonstrated.
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