Date of Award
2001
Document Type
Honors Thesis (Open Access)
Department
Colby College. Chemistry Dept.
Advisor(s)
Bradford P. Mundy
Second Advisor
Dasan Thamattor
Third Advisor
Stephen Dunham
Abstract
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.
Keywords
Natural products -- Synthesis, Aromatic compounds -- Synthesis, Chemistry -- Experiments
Recommended Citation
Bizier, Nicholas P., "Exploratory chemistry in route to aromatic natural products" (2001). Honors Theses. Paper 33.https://digitalcommons.colby.edu/honorstheses/33
Copyright
Colby College theses are protected by copyright. They may be viewed or downloaded from this site for the purposes of research and scholarship. Reproduction or distribution for commercial purposes is prohibited without written permission of the author.