1.  Total Synthesis of Natural Products

We are engaged in the total synthesis of biologically and pharmaceutically important natural products using newly developed synthetic strategies. Representative targets include:

• SCH 71450, a pharmaceutical formulation used for the treatment of attention deficit hyperactivity disorder (ADHD);
• Ribulose-5-phosphate and Xylulose-5-phosphate, key intermediates in the human pentose phosphate pathway;
• Tamaractam, an active component of traditional Chinese medicine with potential therapeutic effects against rheumatoid arthritis.

2. Development of New Synthetic Methodologies in Organic Synthesis

    (a) Carbonyl Translocation Strategy

We have developed carbonyl translocation methodologies to transform inexpensive carbohydrate raw materials into valuable and rare synthetic building blocks, carbohydrates, and biologically active molecules, including:

• 2-deoxy-L-ribose
• 3-deoxy-L-fructose
• D-ribulose
• D-xylulose
• L-deoxyribonucleosides
• 2-deoxy-4′-thio-D-xylosides

    (b) Radical Cascade Reactions

Cascade radical reactions have been developed to achieve vinyl radical ipso-cyclization and 1,4-aryl migration processes. These methodologies have been applied to the synthesis of structural scaffolds found in natural products and pharmaceuticals, such as:

• β-aryl-γ-lactams
• Unsaturated β-aryl-γ-lactams

3. New Drug Synthesis

Newly developed synthetic methodologies are applied to the synthesis of known drugs and biologically active organic molecules, including:

• Telbivudine (L-dT, SEBIVO™, Novartis), a next-generation antiviral drug for the treatment of hepatitis B;
• Rolipram, a phosphodiesterase-4 (PDE4) inhibitor with antidepressant and anti-Alzheimer’s disease activities;
• Phenylpiracetam (Phenotropil), a drug used for the treatment of depression and dementia;
• Phenylpiracetam hydrazide (Fonturacetam hydrazide), which exhibits anticonvulsant activity.

4. Medicinal Chemistry

Our medicinal chemistry research focuses on the design and synthesis of drug-like organic molecules, including:

• Organic ligands targeting neuropeptide FF (NPFF) receptors as alternatives to opioid receptor antagonists, aimed at the development of novel analgesics (painkillers);
• Design, synthesis, and lead modification of organic molecules with therapeutic potential for acute respiratory distress syndrome (ARDS).

5. Controlled Living Radical Polymerization and Biomedical Applications

We develop controlled living radical polymerization techniques for the synthesis of functional glycopolymers. In particular, carbohydrate-based polymer monomers containing tumor-associated carbohydrate antigens (TACAs) are designed and synthesized. These monomers are polymerized to produce glycopolymers bearing cancer-related antigens, such as Tn glycoconjugate polymers, with the goal of mimicking synthetic carbohydrate-based anticancer vaccines.