pet molecule paper

pet molecule paper - Ellyn Velasco Dr. Hauser CHE 341...

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Ellyn Velasco Dr. Hauser CHE 341 October 22, 2007 Taiwaniaquinol B Taiwaniaquinol B (1) is found from Taiwania cryptomeriodes , a Taiwanese pine tree. i This compound could be valuable to the treatment of estrogen-dependent cancers, like breast cancer, prostate cancer, and ovarian cancer among others. ii The strategy of this synthesis is to demonstrate the ability of Meldrum’s acid to be an acylating agent for nucleophiles through intramolecular Friedel-Crafts acylation. The synthesis of this compound begins with 3,5-dihydroxybenzoic acid (5). Bromine and acetyl alcohol brominate the benzoic acid to prepare the compound for a α -substitution. The bromine can only attach to the para position from the carboxylic acid because the alcohols attached to the ring are ortho directing and that spot is less hindered than the spot next to the carboxylic acid. In this same step, sulfurous dimethyloxide [(MeO) 2 SO 2 ] in an acetone solvent and potassium carbonate as a drying agent methylates the alcohol oxygens to esters. The
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This note was uploaded on 04/27/2008 for the course CHE 341 taught by Professor Hauser during the Fall '07 term at Centre College.

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pet molecule paper - Ellyn Velasco Dr. Hauser CHE 341...

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