Standard syllabus
Advanced synthesis · Graduate · Chemistry
Topics
Retrosynthetic analysis
- Disconnection approach and synthon concept
- Functional group interconversions (FGI)
- Strategic bonds and key disconnections
- Convergent vs linear synthesis planning
- Protecting group strategies for complex targets
- Stereochemical planning and chiral pool approaches
- Complexity-building reactions in retrosynthesis
- Computer-assisted retrosynthesis tools (overview)
- Evaluation of synthetic efficiency: step count, yield, scalability
- Literature precedent searching for synthetic routes
C–C bond formation methods
- Palladium-catalyzed cross-coupling: scope and limitations
- Nickel, copper, and iron catalyzed couplings
- Olefin metathesis in total synthesis
- C–H activation and directed functionalization
- Photoredox catalysis in synthesis
- Radical-based C–C bond formations
- Organocatalytic enantioselective reactions
- Asymmetric aldol, Mannich, and Michael additions
- Cycloadditions: Diels–Alder, dipolar, [2+2]
- Metal-catalyzed cyclization cascades
Heteroatom and functional group chemistry
- Selective oxidation and reduction methods
- Baeyer–Villiger, epoxidation, and dihydroxylation
- Amination and amination strategies (Buchwald–Hartwig, etc.)
- Fluorination and halogenation methods
- Glycosylation and oligosaccharide synthesis
- Peptide and macrocycle synthesis strategies
- C–N, C–O, C–S bond formation in complex settings
- Late-stage functionalization of advanced intermediates
- Boron and silicon chemistry in synthesis
- Click chemistry and bioorthogonal ligation in synthesis
Total synthesis case studies
- Classical total syntheses: strychnine, reserpine, morphine
- Modern approaches: palau'amine, brevetoxin, vinigrol
- Natural product-inspired methodology development
- Structure revision through total synthesis
- Biosynthetic pathway-inspired synthesis
- Diversity-oriented synthesis (DOS)
- Fragment coupling strategies for macrocycles
- Solid-phase and flow synthesis of complex molecules
- Scale-up challenges in total synthesis targets
- Critique of published syntheses: efficiency and innovation
Pricing
Graduate-level rates are set on consultation. See the pricing page for K–12 and undergraduate rates.