Chemistry 411: Chemistry and Synthesis of Natural Products

Professor:

Jennifer A. Love (A231,  )

Office Hours:

Wednesday 2-4 pm, A231 (Tentative)

Prerequisites:

For UBC Undergrads: Chem 203; Chem 204; Chem 330 or 313 (330 preferred). For Graduate Students: Strong foundation in undergraduate organic chemistry

Textbooks:

No required textbooks.  Handouts will contain reference to the primary literature.

Reference Texts:

• E.V. Anslyn and D.A. Dougherty, Modern Physical Organic Chemistry, (2006)
• Carey, F. A., Sundberg, R. J. Advanced Organic Chemistry, Part A and B (2000)
• March, J. Advanced Organic Chemistry (1992)
• Kurti, L., Czako, B.Strategic Applications of Named Reactions in Organic Synthesis(2005)
• Corey, E. J., Cheng, X. -M, The Logic of Chemical Synthesis (1989)
• Nicolaou, K. C., Sorensen, E. J. Classics in Total Synthesis (1996)
• Paquette, L. A., Ed. Encyclopedia of Reagents for Organic Synthesis (1995)
• Trost, B. M., Flemming, I., Eds. Comprehensive Organic Synthesis (1991)

Journal:

You will be expected to read organic synthesis papers in the following journals:

• Journal of the American Chemical Society (synthesis-related papers)
• Angewandte Chemie International Edition (synthesis-related papers)
• Organic Letters
• Journal of Organic Chemistry

Problem Sets:

There will be periodic problem sets that complement material covered in lecture and introduce new concepts not covered during class. Answers to these problem sets will be posted on the course website. Students may be examined on material contained within the problem sets.

Comments on the 411/566 split:

Chem 566 students have additional course requirements.
In addition to the standard course material, Chemistry 566 students will have additional examination questions and a written project (details below).

Project (566 only):

  Choose two total synthesis papers on the same natural product. Analyze each route, identify the key steps, and write a report explaining important aspects of these syntheses. Details will be provided later.

Grading:

There will be two exams (midterm and final).

Course Contents (Tentative)

Introduction/Key Concepts of Synthesis

Fundamental Principles

• Bonding
• pKa values of organic acids, particularly C-H acids
• Common bases and solvents, aprotic solvents
• Composition-equilibrium-free-energy relationships
• Temperature effects
• Bond energies
• Conformation: acyclic and cyclic

Functional Group Interconversions

• Oxidations
• Reductions
• Protecting groups

C-C Bond Formation

• Reactivity of Enols/Enolates/Enamines/Metalloenamines
• Aldol Reaction
• Allylations
• Advanced Carbonyl additions
• Mannich Reaction
• Imine allylation
• Conjugate Addition reactions
• Cross-coupling

C=C Bond Formation

• Coupling Reactions
• C=C and alkyne bond forming reactions

Radical Reactions

Pericyclic and Sigmatropic Reactions

Enantioselective Synthesis (if time)