Date of Award
Honors Thesis (Open Access)
Colby College. Chemistry Dept.
Bradford P. Mundy
This research has focused on the total synthesis of the iron--chelating natural product 1-(2,3-hydroxyphenyl)-4-methoxy-I-butanone. An extract of the iron-cleficient fungus Gleophyllwn lraebeum, this molecule is thought to bind to Fe3+ in a hexacoordinate system to aid in transport through cell walls in order to help regulate iron levels in such iron-deficient fungi. Since the proposed structure of the molecule is based only on the spectral data of a very small sample, our hope is to synthesize and confirm its structure as the extract of the brown rot fungus. We have developed a relatively short retrosynthesis for our work on this molecule. Our approach relies on an electrophilic aromatic substitution of the side chain onto the aromatic ring of the catechol. By building up the ether side chain in the first few steps of the synthesis, we will be able to add it to the catechol as an acid chloride through a Friedel-Crafts acylation. This approach will allow us to avoid the use of protecting groups for the reactive dial system; such methods have proved problematic in past work done by our group.
1-(2, 3-hydroxyphenyl)-4-methoxy-I-butanone, iron-chelating natural product, Gleophyllum traebeum, retrosynthesis, electrophilic aromatic substitution, Friedel-Crafts acylation, protecting groups
Recommended CitationWeber, Michelle E., "A Catechol Approach to Natural Product Synthesis" (2000). Honors Theses. Paper 340.
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