Publication Date
2013
Document Type
Thesis
Committee Members
William Feld (Advisor), Daniel Ketcha (Committee Member), Kenneth Turnbull (Committee Member)
Degree Name
Master of Science (MS)
Abstract
The synthesis of the arylnaphthalene lignan haplomyrtin using vanillin as a starting material is synthesized via: 1) a bromination of vanillin, 4-hydroxy-5-methoxybenzaldehyde, to produce 6-bromovanillin 2) a hydroxyl protection step of 6-bromovanillin with triisopropylsilylchloride to produce 2-bromo-4-triisopropylsilyoxy-5-methoxybenzaldehyde 3) an aldehyde protection step through a cyclic acetal formation using ethylene glycol to produce 2-(2-bromo-4-triisopropylsilyloxy-5-methoxyphenyl)-1,3-dioxolane 4) a lithium for halogen exchange of the doubly protected 6-bromovanillin leads to neucleophilic coupling with piperonal producing 1,3-benzodioxol-5-yl-[5-triisopropylsilyloxy-2-(1,3-dioxolane-2-yl)-4-methoxyphenyl]methanol and 5) an acid catalyzed intramolecular cycloaddition /Diels Alder adduct with dimethyl acetylenedicarboxylate producing dimethyl 1-(1,3-benzodioxol-5-yl)-4-hydroxy-6-methoxy-7-triisopropylsilyloxynaphthalene-2,3-dicarboxylate.
Page Count
60
Department or Program
Department of Chemistry
Year Degree Awarded
2013
Copyright
Copyright 2013, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
