Global Chlorination: A General Synthetic Strategy towards Chlorosulfolipid Natural Products

路易斯安那州立大学的Rendy Kartika教授在化学部化学合成计划的资助下，研究了立体化学复杂的脂肪族多元醇转化为相应的烷基多氯化物。除了将新的氯化技术引入有机反应工具箱外，这项研究还为学生研究人员提供了宝贵的教育经验，使他们能够在STEM劳动力中具有竞争力。 该项目的资助加强了Kartika教授为培训来自代表性不足的群体和妇女的学生所做的既定努力，并帮助在路易斯安那州立大学建立有机合成。 这项工作的更广泛的影响得益于两个外展活动：1）路易斯安那州立大学化学演示项目，和2）路易斯安那州有机化学研讨会（LOCS）。ChemDemo是一个既定的服务学习活动，直接暴露在大型普通化学课程就读路易斯安那州立大学的本科生动手化学实验进行的K-12学生在巴吞鲁日地区。 LOCS是一个为期一天的研讨会，教授卡蒂卡在路易斯安那州立大学成立于2013年，并在2016年重复。 该活动汇集了海湾南部地区的化学研究生和本科生，以扩大当代有机化学研究的传播，其智力价值集中在制定一项可行的总战略，实现氯硫脂及其同系物的全合成。由于涉及多氯代烃的立体选择性反应的知识存在差距，氯硫脂复杂的结构特征对结构解析和全合成提出了重大挑战。该策略建立在以立体选择性方式将立体互补的脂肪族1，2-和1，3-二醇转化为它们各自的1，2-和1，3-二氯化物的合成方法上。 本研究继续设计收敛合成的氯磺脂天然产物丹尼克酰胺在A，突出了全球氯化相应的多元醇前体的关键步骤，在全合成。

AbstractIn 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.