Abietic acid in the synthesis of unnatural alkaloids
Gale-Day, Zachary John
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The synthesis of unnatural alkaloid-type products from abietic acid was explored. In order to synthesize these products the protection of the carboxylic acid was achieved followed by a selective dihydroxylation of the C-ring was followed by oxidative diol cleavage. Using the dione yielded a reductive aminocyclization followed. This reaction was first explored using 4-methoxybenzylamine and after optimization the alkaloid-type product was synthesized in a 34% yield. Using the optimized conditions a small library of analogues were synthesized utilizing different primary amines.
Honors Thesis, BA in Chemistry 2014