Green syntheses of 2-naphthol-based oxapolycycles
LE3 .A278 2011
Master of Science
A review of one‐step cyclization reactions on 2‐naphthol is described in a comprehensive manner, organized by reaction type/class. This is significant, as the following work deals with one‐step cyclizations on a 2‐naphthol framework. Splitomicin analogues were synthesized under green reaction conditions in a microwave‐reactor, and characterized through all standard spectral means. This synthesis is a landmark in microwave chemistry, as four components react to give the desired product in five tandem steps, with good yield. Oxidation of these products affords the lactone analogue to splitomicin. Biological activity of these molecules has yet to be determined. Under solvent‐free conditions, 2,2‐disubstituted acetaldehydes react with 2‐naphthol and a catalytic amount of pTSA, under microwave conditions to afford 2,2‐disubstituted dihydronaphthofurans in good to excellent yields.
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