School of Science Department of Chemistry 11 Synthesis of Useful Organic Molecules Supervisor: SUN Jianwei / CHEM Student: LEE Hoi Cheuk / CHEM-IRE Course: UROP 1000, Summer Many chemical compounds are useful in research, but unfortunately they are not commercially available. Thus, the synthesis of these useful organic molecules need to take place and is thus the focus of this project. Chemicals are first synthesized from several commercially available substances to those that are required in research, which is later on reacted in other methods to study their reactivity. Via various chemical reactions, the said synthesis can be done. Thus, in this report, the methods of synthesis and purification for these commercially unavailable compounds will be included in a fashion similar to those in the Supporting Information. Green Chemistry in Organic Synthesis Supervisor: TONG Rongbiao / CHEM Student: LU Yuheng / CHEM-IRE Course: UROP 1100, Summer Chiral phosphoric acids have emerged as a new class of highly efficient and enantioselective Brønsted acid organic catalysts in recent years. They have been successfully applied in catalyzing a variety of important organic synthetic reactions, including asymmetric Mannich reactions, reductive aminations, Pictet-Spengler reactions, aza-Diels-Alder reactions, and aza-Ene reactions. Chiral phosphoric acid catalysts are both Lewis basic and Brønsted that can simultaneously activate both electrophilic and nucleophilic substrates. As a new class of bifunctional organic catalysts, chiral phosphoric acids exhibit high catalytic activity and enantioselectivity, with catalyst loadings as low as 0.05 mol% according to previous report. In this study, the researcher conducted a stepwise synthesis of the chiral BINOL-derived phosphoric acid catalyst, which is originally designed for aza-Friedel-Crafts asymmetric reactions. Green Chemistry in Organic Synthesis Supervisor: TONG Rongbiao / CHEM Student: MA Muyang / CHEM Course: UROP 2100, Fall UROP 3100, Spring In this report, we focus on the total synthesis of (-)-Fusarisetin A based on synthetic route of Xu. This study presents a modified total synthesis of (-)-Fusarisetin A based on the nature-inspired approach. The original nine-step synthesis from (S)-(-)-citronellal has been modified by introducing alternative reactions. The key transformations of the synthetic route include a stereoselective intermolecular Diels-Alder reaction for the construction of the decalin moiety. The revised route offers a concise and efficient strategy for the synthesis of (-)-Fusarisetin A and opens up possibilities for the total synthesis of analogues for further biological evaluation and other possible reactions.
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