Chemistry 566: Chemistry and Synthesis of Natural Products

Professor: Glenn Sammis (A349, gsammis@chem.ubc.ca)

Office Hours: Wednesday 2-4 p.m., A349 (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:  (available in the main library unless otherwise indicated)

• Carey, F. A., Sundberg, R. J. Advanced Organic Chemistry, Part 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)*

* Science Division of the Main Library

Chem 566 Reading:  You will be expected to read the following journals of organic synthesis:

• 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, which will be worth 10% of your grade.
Problem sets will both 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: Chemistry 556 students have additional course requirements beyond Chem 411 
(Chemistry 411 students may have the option of these for extra course credit).  In addition to the standard course material, Chemistry 556 students will have (a) additional examination questions, (b) additional required reading, and (c) 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 midterms and a final.  If all problem sets are turned in with a passing average, 
then a passing grade on the final guarantees a passing grade in the course.

 Course Contents (Tentative)

Introduction/Key Concepts of Synthesis

Fundamental Principles

• 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

C=C Bond Formation

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

Transition Metal Catalyzed Coupling Reactions

Radical Reactions

Pericyclic and Sigmatropic Reactions

Enantioselective Synthesis (if time)