Nature Product Total Synthesis

Here in the Wuest Lab, we focus on the total synthesis and biological investigation of several underexplored natural products with promising futures as antimicrobial agents. We use cutting-edge, state-of-the-art synthetic methods to access these complex molecules. In the past, we have completed the syntheses of multiple natural products, such as carolacton, promysalin, mindapyrrole A, and baulamycins A and B. In addition to these total syntheses, we have prepared several synthetically simplified analogs that maintain (or increase) antimicrobial activity. Current efforts towards multiple natural products and analog design are underway.

Publications

1. Steele, A.D.; Knouse, K.W.; Keohane, C.E.; Wuest, W.M.* “Total Synthesis and Biological Evaluation of (-)-Promysalin” J. Am. Chem. Soc. 2015 137, 7314. DOI: 10.1021/jacs.5b04767

2. Steele, A.D.; Ernouf, G.; Lee, Y-E.; Wuest, W.M.* “Diverted Total Synthesis of the Baulamycins and Analogues Reveals an Alternate Mechanism of Action” Organic Letters 2018 20, 1126 DOI: 10.1021/acs.orglett.8b00054

3. Solinski, A.E.^#; Koval, A.B.^#; Brzozowski, R.S.^#; Morrison, K.R.; Fraboni, A.J.; Carson, C.E.; Eshraghi A.R.; Zhou, G.; Quivey, R.G.; Voelz, V.A.; Buttaro, B.A.; Wuest. W.M.* “Diverted Total Synthesis of Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in Streptococcus mutans Biofilms” J. Am. Chem. Soc. 2017139, 7188. DOI: 10.1021/jacs.7b03879

4. Shapiro, J.A.^#; Morrison, K.R.^#; Chodisetty, S.S.; Musaev, D.G.; Wuest, W.M.* “Biologically Inspired Total Synthesis of Ulbactin F, an Iron-Binding Natural Product” Org. Lett. 2018 20, 5922. DOI: 10.1021/acs.orglett.8b02599