Global Chlorination: A General Synthetic Strategy towards Chlorosulfolipid Natural Products

Louisiana State University, Baton Rouge LA

Investigators

Abstract

Abstract In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Rendy Kartika of Louisiana State University (LSU) is investigating the conversion of stereochemically complex aliphatic polyols to the corresponding alkyl polychlorides. In addition to introducing new chlorination technology to the toolbox of organic reactions, this research provides invaluable educational experience for student researchers, empowering them to be competitive in the STEM workforce. Funding of this project strengthens Professor Kartika's established efforts to train students from underrepresented groups and women, and help build organic synthesis at LSU. The broader impact of this work benefits from two outreach activities: 1) the LSU ChemDemo project, and 2) the Louisiana Organic Chemistry Symposium (LOCS). ChemDemo is an established service-learning activity that directly exposes LSU undergraduates enrolled in large general chemistry courses to hands-on chemistry experiments performed for K-12 students in the Baton Rouge area. LOCS is a one-day symposium that Professor Kartika established at LSU in 2013 and is repeating in 2016. The event brings together chemistry graduate and undergraduate students in the Gulf South region to broaden dissemination of contemporary organic chemistry research. The intellectual merit is focused on developing a viable general strategy towards the total synthesis of chlorosulfolipids and their congeners. Due to the gap in the knowledge concerning stereoselective reactions involving polychlorinated hydrocarbons, the complex structural features in chlorosulfolipids present significant challenges for structural elucidation and total synthesis. The strategy builds on synthetic methods that convert stereocomplementary aliphatic 1,2- and 1,3-diols to their respective 1,2- and 1,3-dichlorides in a stereoselective manner. This study continues with the design of convergent synthesis of chlorosulfolipid natural product danicalipin A, highlighted by global chlorination of the corresponding polyol precursor as the key step in the total synthesis.