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Synthesis of a Novel Tocopherol/Carotenoid Derivative
Norwegian University of Science and Technology, Faculty of Natural Sciences and Technology, Department of Chemistry.
2012 (English)MasteroppgaveStudent thesis
Abstract [en]

The goal of this work is the synthesis of a tocopherol/carotenoid hybrid derivative (1, figure II). The novel derivative is believed to exhibit synergistic antioxidant effects between its chromanol and polyene consituents. The synthesis of 1 was completed up to and including the immediate precursor 12. Commercially avaliable Trolox (7) was reduced by Red-Al® to 8 (step a) in 95% yield. Chromanol aldehyde 9 was formed by Swern oxidation of 8 in 65% yield (step b). Wittig reaction between 9 and phosphonium salt 10 afforded 11 in 33% yield and varying cis : trans ratio (step c), and subsequent elongation produced 12 (14% yield, step d). The Wittig reactions were performed with reflux and microwave irradiation. Various attempts at protecting the phenolic group in intermediate 8 by silylation or benzylation did only lead to formation of 8B. Oxidation of 8 by the Dess-Martin oxidation formed the unexpected quinone-like derivative 27. Efforts to protect the phenolic group in intermediate 9 by benzoylation and silylation only produced 9A, found to be unsoluble in all common laboratory solvents.

Place, publisher, year, edition, pages
Institutt for kjemi , 2012. , 176 p.
Keyword [no]
ntnudaim:6705, MKJ Kjemi, Organisk kjemi
URN: urn:nbn:no:ntnu:diva-16805Local ID: ntnudaim:6705OAI: diva2:536474
Available from: 2012-06-21 Created: 2012-06-21

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