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Total synthesis of barettin: Model study of specialized aldol condensation to directly access diketopiperazine targets

Kelley, Elizabeth W
Abstract
We synthesized (±)-(Z)-barettin, a potent anti-biofouler, with 31 % yield as a mono-TFA salt over seven steps with only one chromatographic separation. The route is efficient, proceeds under mild conditions, and is optimized to reduce formation of undesired byproducts otherwise seen in the aldol condensations and the Boc protection. Our route enables us to 1) utilize a DKP condensation with an unstable aliphatic aldehyde, 2) showcase how the DKP condensation provides direct access to a bioactive scaffold, and 3) suggest a simple, high yielding route to barettin and analogues consisting of only one chromatographic separation.
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2017-05-01
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Undergraduate Honors Theses
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Scheerer, Jonathan
Harbron, Elizabeth
Hinkle, Robert
Allen, Jonathan
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Chemistry
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https://scholarworks.wm.edu/handle/internal/10466
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