Because of the time, resources, and instrumentation required, most campaigns to synthesize natural products are fought on the battlefields of Ph.D.-granting institutions. Nevertheless, talented and devoted undergraduate researchers at teaching-focused universities can and do make prominent contributions to peer-reviewed publications that feature total synthesis. Pursuing the total synthesis of bioactive marine natural products with undergraduates provides ample opportunities to teach foundational research techniques that translate to the real world. These skills include an awareness and practice of lab safety, experimental reproducibility, the ethical conduct of research, gathering and analyzing data, as well as effective science writing and presentation. Together, these experiences comprise a capstone for the undergraduate curriculum in the chemical sciences.<br/><br/>Marine natural products are intriguing targets for laboratory preparation. Access to quantities of a bioactive natural compound can facilitate the discovery of additional biological targets and the elucidation of the molecule's specific chemical mechanism of action. Furthermore, challenges encountered during the preparative effort can promote the development of enabling synthetic methodology. In particular, application of a direct guanidinylation approach, in lieu of extant guanidinylation methods, was a breakthrough that led to the first total synthesis of the selective, blood coagulation Factor XIa inhibitors clavatadine A and B, and established the shortest approach to prepare anti-cancer, anti-CNS natural products phidianidine A and B. Each total synthesis was completed by undergraduates and the PI at a teaching-intensive, primarily undergraduate institution.

Direct, early stage guanidinylation as an enabling strategy for the total synthesis of bioactive marine natural products

250th National Meeting (2015)

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