A5025696015- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Synthetic Organic Chemistry Methods
- Carbohydrate Chemistry and Synthesis
- Microbial Natural Products and Biosynthesis
- Oxidative Organic Chemistry Reactions
- Catalytic C–H Functionalization Methods
- Advanced Synthetic Organic Chemistry
- Chemical synthesis and alkaloids
- Alkaloids: synthesis and pharmacology
University of California, Berkeley
2023
University of Oxford
2023
Herein, we describe the convergent enantioselective total synthesis of himalensine A in 18 steps, enabled by a highly enantio- and diastereoselective construction morphan core via palladium/hydroxy proline co-catalyzed desymmetrization vinyl-bromide-tethered cyclohexanones. The reaction pathway was illuminated density functional theory calculations, which support an intramolecular Heck situ-generated enamine intermediate, where exquisite enantioselectivity arises from carboxylate...
Herein, we describe our synthetic efforts toward the pupukeanane natural products, in which have completed first enantiospecific route to 2-isocyanoallopupukeanane 10 steps (formal synthesis), enabled by a key Pd-mediated cyclization cascade. This subsequently facilitated an unprecedented bio-inspired "contra-biosynthetic" rearrangement, providing divergent access 9-isocyanopupukeanane 15 synthesis). Computational studies provide insight into nature of this rearrangement.
Abstract Herein, we describe our synthetic efforts toward the pupukeanane natural products, in which have completed first enantiospecific route to 2‐isocyanoallopupukeanane 10 steps (formal synthesis), enabled by a key Pd‐mediated cyclization cascade. This subsequently facilitated an unprecedented bio‐inspired “contra‐biosynthetic” rearrangement, providing divergent access 9‐isocyanopupukeanane 15 synthesis). Computational studies provide insight into nature of this rearrangement.