Synthesis of novel 6-deoxyanthracyclines
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
An extremely direct route to the 6-deoxyanthracycline skeleton is described. The initial route to quinone 10 failed due to an unexpected complication in the Ago demethylation step. However, starting from 2-bromo- 1,4-dimethoxynaphthalene, furan 17 could be prepared in two steps. Furan 17 was then converted into anthraquinone 19 in five steps. The eight-step route proceeds in 9% overall yield.
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Reprinted (adapted) with permission from The Journal of Organic Chemistry, 50(18); 3252-3255. Doi: 10.1021/jo00218a002. Copyright 1985 American Chemical Society.