CHM342F: Modern Organic Synthesis

Instructor

Professor Mark Lautens (mlautens@chem.utoronto.ca)
Office: Davenport Wing Rm. 357, Phone: 416-978-6083
Office Hours: M 2-4pm, T 4-5pm. W 2-4 or by appointment

Prerequisite CHM247/249 or equivalent course

Text :

“Organic Chemistry” Clayden, Greeves, Warren, &Wothers

Course Web-page and e-mail:

Attendance at lectures is expected and necessary for success in this course. The web-page will provide information on test dates, an outline of the course and copies of any handouts given in class. Lecture notes will not appear on the web. I am available by e-mail to schedule appointments and to ask questions. I may elect to respond to your question in class if we have a class the next day so that others with similar problems can benefit from the additional discussion. I generally respond quickly to e-mail unless I am out of town. It may not be possible to respond in time to questions sent the night before or the day of the tests so start studying well in advance of the term tests.

Molecular Models : Strongly recommended and available at the bookstore

Topics : This course provides an overview of the key reaction classes as they relate to reactivity, selectivity and utility in the synthesis of organic molecules. We will begin by reviewing key concepts from early courses in organic chemistry, move on to discuss different types of selectivity, retrosynthesis and devote most of our time to learning new reactions that will be used to make increasingly complex natural products and bioactive compounds with medicinally interesting properties.

1. Introduction and review (Chpt 1, 2 & 30)
2. Cycloadditions, rearrangements and eliminations (Chpt 35, 36 & 37)
3. Carbon acids and bases (Chpt 21, 27, 28 & 29)
4. Alkylations and Carbonyl additions (Chpt 26 & 34)
5. Organo-main group chemistry (Chpt 47)
6. Organometallic chemistry (Chpt 48)

The assignment will require you to compare and contrast two synthetic routes to a target molecule with biological activity. A list of suggested molecules will be provided by the half way point of the course. You will make a short presentation to me then we will discuss the routes in an oral examination in the last week of classes.

Note: Last date to drop the course without penalty is November 4, 2007.