Date of Award
Honors Thesis (Open Access)
Colby College. Chemistry Dept.
Bradford P. Mundy
The focus of this research was the synthesis of two natural products, 1-methyl-s-(1,2,2-trimethy1cyclopentyl)-benzene (formally cuparene), and 3-(1,2dimethylcyclopenty1)-5-methylbenzene-l,2-diol (formally herbertene diol). Cuparene possesses anti-fungal and anti-arthritic properties. This molecule has been the target of a number of syntheses. Herbertene diol, a natural product itself, represents one retrosynthetic step back from mastigophorane; a compound isolated form the liverwort Mastigophora diaclolades. Mastigophorane has been shown to have neural network forming capabilities and has warranted complete synthetic efforts. Through the same chemistry involve in the formation of cuparene, we sought a route to herbertene diol in two steps. We report a successful route to the synthesis of cuparene in its racemic form. We also report the successful synthesis of an analog of herbertene diol, as well as the proof that our concept can be used to add sterically congested systems to aromatic rings through the use of Friedel-Crafts alkylation methods.
Natural products -- Synthesis, Aromatic compounds -- Synthesis, Chemistry -- Experiments
Recommended CitationBizier, Nicholas P., "Exploratory chemistry in route to aromatic natural products" (2001). Honors Theses. Paper 33.
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