2. Instructor Information
3. Course Objectives
This course will focus on the design and synthesis of organic compounds, including natural products, with an emphasis on modern synthetic methodologies, reaction mechanisms, and stereochemistry. In addition, to foster students' ability to orchestrate organic reactions, each student will be required to present a literature seminar on a natural product synthesis and also a project involving a retrosynthetic analysis of a selected natural product.
4. Prerequisites & require
Organic Chemistry I/II, preferred
5. Grading
(1) Literature seminar: 30%
(2) Retrosynthetic analysis project: 30%
(3) Assignments/quiz/exam: 30%
(4) Attendance: 10% (*5 absences will result in failure of the course)
6. Course Materials
| Title |
Author |
Publisher |
Publication
Year/Edition |
ISBN |
|
Classics in Total Synthesis
|
K.C. Nicolaou, E.J. Sorensen
|
VCH, Weinheim
|
1996
|
|
|
Classics in Total Synthesis Ⅱ
|
K.C. Nicolaou, S.A. Snyder
|
Wiley-VCH, Weinheim
|
2003
|
|
|
Modern Methods of Organic Synthesis
|
Carruthers, W.; Coldham, I.
|
Cambridge, University Press
|
2004
|
|
|
The Logic of Chemical Synthesis
|
E.J. Corey, X.-M. Cheng
|
John Wiley & Sons, N.Y.
|
1989
|
|
7. Course References
1. Bruckner, R. “Advanced Organic Chemistry, Reaction Mechanisms”, Harcourt, NY, 2002
2. Comprehensive Organic Chemistry, by Barton and Ollis (Ed.), vol.1-6, Pergamon, 1979
3. Comprehensive Organic Synthesis, B. M. Trost Ed., Vol. 1-9, Pergamon, 1991
4. K. C. Nicolaou, E. J. Sorensen, “Classics in Total Synthesis”, VCH, Weinheim, 1996.
5. K. C. Nicolaou, S. A. Snyder, “Classics in Total Synthesis II”, Wiley-VCH, Weinheim, 2003
6. Journal Articles from J. Am. Chem. Soc., Angew. Chem. Int. Ed., Chem. Commun., and Organic Letter, etc.
8. Course Plan
1. Introduction to Synthesis
2. Oxidation
3. Vicinal Dihydroxylation
4. Oxidative Cleavage Reactions
5. Epoxidation Reactions
6. Catalytic Hydrogenation
7. Reduction with Hydrides
8. Dissolving Metal Reduction
9. Formation and Alkylation of Enolates
10. Alkylation of Other Nucleophilic Agents
11. Activation of Hydroxyl and Carboxyl Groups
12. Carbonyl Condensation Reactions
13. Carbonyl Olefination Reactions
14. Alkene Formation Reactions
15. Alkene Addition Reactions
16. Alkene Metathesis
17. Alkynes
18. Pericyclic Reactions
19. [4+2] Cycloaddition Reactions
20. [3+2] Cycloadditions
21. [2+2] Cycloadditions
22. [2+1] Cycloadditions
23. Ene Reactions
24. Chemistry of Organoboron Compounds
25. Chemistry of Organosulfur and Selenium Compounds
9. Course Operation
- Lecture materials will be provided as ppt or pdf files
- Guidelines for the literature seminar and presentation project will be given
- The retrosynthetic project will be conducted through steps: 1) selection of the target molecule, 2) identification of key steps, 3) detailed synthetic steps, and 4) finalization of the retrosynthetic analysis. Students are supposed to have discussions with Professor at each step.
- The lecture will be given in English
10. How to Teach & Remark
This course is recommended for the graduate/undergraduate students who have strong background in Organic Chemistry.
11. Supports for Students with a Disability
- Taking Course: interpreting services (for hearing impairment), Mobility and preferential seating assistances (for developmental disability), Note taking(for all kinds of disabilities) and etc.
- Taking Exam: Extended exam period (for all kinds of disabilities, if needed), Magnified exam papers (for sight disability), and etc.
- Please contact Center for Students with Disabilities (279-2434) for additional assistance