Date Thesis Awarded

5-2017

Document Type

Honors Thesis

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Jonathan Scheerer

Committee Member

Elizabeth Harbron

Committee Member

Robert Hinkle

Committee Member

Jonathan Allen

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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