CHEMISTRY 451 - Organic Chemistry III Course Outline Fall 201 ...

CHEMISTRY 451 - Organic Chemistry III Course Outline Fall 201 Instructor: Dr. Kevin D. Moeller Office: Louderman 440 (Enter through L 438) Labs: McMillen 406 and 408 Office Hours: M 1-2 PM, W 12-1 PM, Th 11:00-12:00 AM, F 2:00-3:00 I will also be available by appointment. Unscheduled visits are fine, however, please be aware that my ability to respond to such visits is subject to prior commitments and other pressures on my time. Book: Smith, M; March, J. March’s Advanced Organic Chemistry, 6th ed., John Wiley and Sons; New York, 2007. Recommended: Scudder, P. H. Electron Flow in Organic Chemistry, John Wiley and Sons, Inc.; New York, 1992. Grading: The course will consist of three take home exams (100 pts. each) and an in-class final exam (100 points). The exams are tentatively scheduled for the following dates: Exam Exam Exam

I – Oct. 7 II – Nov. 4 III – Dec. 9

The exams will cover the material discussed in class, reading assigned from the text and literature, and homework problems. Homework (m ainly in the form of practice exams) will be given throughout the course. It will not be collected or graded. The in-class final exam will be based on material taken from the midterm exams. Cancelled Classes: Unfortunately, I have a pair of commitments that will lead to three classes being cancelled. The dates are September 7th, September 9th, and September 23. Course Description: Modern organic chemistry is often viewed as involving hundreds of individual reactions. Each of these reactions has its’ own particular advantages and disadvantages. At first glance it would appear to be an impossible task to grasp even a fraction of the information known about these reactions, especially in a one-semester class. Fortunately, however, many of these reactions can be understood in the context of a few fundamental principles. An understanding of these principles can allow the chemist to develop a "feel" for what kinds of transformations can be done, for how chemical reactions can be controlled, and for how chemistry can be used to selectively piece together molecules with a wide range of architectural diversity. In this course, the synthesis of several complex organic molecules will be examined. These molecules will provide a backdrop for exploring the factors that govern particular transformations within a synthetic sequence, as well as the choice of the overall synthetic route itself. It is hoped that the course will provide students with the foundation needed for independently studying the chemical literat ure, and will serve to build in students an appreciation for the intriguing possibilities organic chemistry offers for custom building molecules.

Initially the plan is to adjust the pace of the class in order to accommodate potential variations in the background of the students. For this reason, only a crude outline of topics is suggested. We will simply get as far as we can, while making sure that topics of fundamental importance are not skimmed over. Crude Course Outline: I. Aphidicolin - Bettolo A. A review of conformational analysis and stereoelectronic control. B. Several basic synthetic methods. II. The Erythronolides - Control of relative and absolute stereochemistry. A. R.B. Woodward - A classic approach! B. Masamune - Acyclic stereocontrol and the Aldol condensation. III. Ophiobolin - Paquette A. Why all the fuss about pericyclic reactions? B. So that is a transannular interaction. IV. Taxol - Wender A. Photochemistry and sigmatropic rearrangements. B. Elegance in synthesis. V. Pumiliotoxin - Trost A. Why organometallic chemistry? B. Sharpless epoxidations. C. Olefin synthesis. VI. Gelsemine - Fukuyama A. Olefination reactions. B. Carbenoids VII. Torreyanic Acid – Porco, Jr. A. A one molecule course review and a chance to tie up loose ends. B. A summary of how to think about transition metal-based reactions. VIII. Salicylihalamide – Snider A. Metathesis chemistry. B. Synthesis of 1,3-diols