Peterson, John Robert
M.S. (Master of Science)
Department of Chemistry
Manganese(III) acetate was utilized in various synthetic schemes directed at biologically active natural and unnatural products. Salicylic acid and cyclopentanone derivatives were obtained by manganese(III) acetate mediated intramolecular cyclization of ω - unsaturated - β -dicarbonyl compounds. Control of the mode of cyclization (ie. closure to five or six-membered ring) by variation in the nature of the radical terminus was achieved. Platelet activating factor (PAF) is a highly potent phospholipid. It has been linked to various biological activities and pathways, making it one of the important mediators of physiological processes. As part of an attempt to discover new antagonists of PAF, a series of trans-4. 5-dihydro-4-acetoxymethyl-2,5-diaryl-3-furancarboxylates were synthesized. These compounds were modeled after the potent PAF-antagonist trans-2.5- bis(3,4,5-trimethoxyphenyl)tetrahydrofuran. Manganese(III) acetate mediated annulation of aroyl acetates onto cinnamyl esters served as the synthetic methodology for preparation of the dihydrofurans. Dihydrofurans, synthesized as potential PAF-antagonists, served as synthetic intermediates in a new route to a class of antileukemic lignan lactones. In a multistep synthetic sequence consisting of saponification, lactonization and then hydrogenation, 2,3-diaryl-3,7-dioxabicyclo[3.3.0]octan-8-ones were prepared. In the case of the 2,3-diphenyl analogue, cis 3,4-dibenzyl-2,3,4,5-tetrahydrofuran was obtained. These compounds are advanced synthetic precursors of a class of antileukemic dibenzocyclooctadienes exemplified by the lignan lactone steganone.
Horsley, David Bramwell, "Synthetic applications of manganese (III) acetate chemistry" (1989). Graduate Research Theses & Dissertations. 5198.
ix, 92 pages
Northern Illinois University
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