Date Thesis Awarded
5-2017
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Jonathan Scheerer
Committee Members
Elizabeth Harbron
Robert Hinkle
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.
Recommended Citation
Kelley, Elizabeth W., "Total synthesis of barettin: Model study of specialized aldol condensation to directly access diketopiperazine targets" (2017). Undergraduate Honors Theses. William & Mary. Paper 1098.
https://scholarworks.wm.edu/honorstheses/1098
