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Syllabus for Chemistry 852 - Spring 2011 (PDF version)

Course content:   "In-depth coverage of the principle reactions leading to carbon-carbon bond formation, along with functional group transformations. Strategies and methods for organic synthesis."

Lecture Times:     Tuesdays & Thursdays 8:30–9:50 am, room 481E Chemistry Building
                               Class Presentations: Saturdays 9-11 am, room 581E Chemistry Building

Course Website:   http://www.chemistry.msu.edu/courses/cem852/index.html   


Instructor:

Professor Robert E. Maleczka, Jr.  
phone: 355-9715 x124
email: maleczka@msu.edu 
office hours: by appointment (540 Chemistry)

Course Secretary:

Ms. Nancy Lavrik
email: lavrik@chemistry.msu.edu 


Required Texts:

        1. Paul Wyatt & Stuart Warren, Organic Synthesis: Strategy and Control, Wiley, 2007.  ISBN-978-0-471-92963-5
        2. George S. Zweifel & Michael H. Nantz, Modern Organic Synthesis: An Introduction, W.H. Freeman, 2007.  ISBN-0-7167-7266-3


Recommended Texts:

        1.  Paul Wyatt & Stuart Warren, Workbook for Organic Synthesis: Strategy and Control, Wiley, 2007.  ISBN-978-0-471-92964-2
        2.  K.C. Nicolaou & E.J. Sorensen, Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996.  ISBN-3-527-29231-4


Dates
Planned Lecture Schedule*
Reading Assignments
January 11
 Course Intro/Review of Physical Data CEM 850
January 13 Introduction to Retrosynthetic Analysis
Wyatt/Warren Chapter 1
January 18 Design of Experiments (DOE)
January 20 Regioselectivity: Controlled Aldol Reactions
 Wyatt/Warren Chapter 3
January 25 Stereoselectivity: Stereoselective Aldol Reactions
 Wyatt/Warren Chapter 4
January 27 Alternative Strategies for Enone Synthesis
 Wyatt/Warren Chapter 5
February 1
 The Synthesis of Cyclopentenones
 Wyatt/Warren Chapter 6
February 3
 The Ortho Strategy for Aromatic Compounds Wyatt/Warren Chapter 7
February 8
 σ-Complexes of Metals Wyatt/Warren Chapter 8
February 10
 Controlling the Michael Reaction Wyatt/Warren Chapter 9
February 15
 Specific Enol Equivalents
 Wyatt/Warren Chapter 10
February 17
 Review
Sat. Feb. 19 (9 – noon)
Exam 1 to be held in room 183
100 pts
February 22 Extended Enolates
 Wyatt/Warren Chapter 11
February 24 Allyl Anions
 Wyatt/Warren Chapter 12
March 1
 Homoenolates Wyatt/Warren Chapter 13
March 3
 Acyl Anion Equivalents Wyatt/Warren Chapter 14
March 15 Synthesis of Double Bonds of Defined Stereochemistry
 		Wyatt/Warren Chapter 15
March 17
 Stereocontrolled Vinyl Anion Equivalents Wyatt/Warren Chapter 16
March 22
 Electrophilic Attack on Alkenes Wyatt/Warren Chapter 17
March 24
 Vinyl Cations:  Palladium-Catalyzed C–C Coupling Wyatt/Warren Chapter 18
March 29
 Allylic Alcohols:  Allyl Cation Equivalents (and More) Wyatt/Warren Chapter 19
March 31 Review
Sat. April 2 (9 – noon)
Exam 2 to be held in room 183
100 pts
April 5
 Controlling Relative Stereochemistry
 		Wyatt/Warren Chapter 21
April 7
 Asymmetric Induction: Reagent-Based Strategy Wyatt/Warren Chapter 24
April 12
 Asymmetric Catalysis: Formation of C–O and C–N Bonds Wyatt/Warren Chapter 25
April 14
 Asymmetric Catalysis: Formation of C–H and C–C Bonds Wyatt/Warren Chapter 26
April 19
 Asymmetric Induction: Substrate-Based Strategy
 Wyatt/Warren Chapter 27
April 21
 Kinetic Resolution
 Wyatt/Warren Chapter 28
April 26
 Enzymes: Biological Methods in Asymmetric Synthesis Wyatt/Warren Chapter 29
April 28
 Review
Thursday May 6
(7:30–11:30 a.m.)		 Final Exam to be held in room 183 150 pts

*The links will take you to the start of the related chapter in Professor William Reusch's Virtual Textbook of Organic Chemistry

Classic Syntheses (50 points):

On most Saturdays two students will each present a synthesis from Nicolaou's "Classics in Total Synthesis" (on reserve in the library).  The presentations will begin at 10 am and take place in room 581E.  Plan for your presentation to take about 30 minutes, excluding questions.  Your lecture will be graded using the same criteria used for the Organic Seminars, including input from your classmates.  I also expect you to provide a  PDF file within one week of your presentation for placement on the web.  (Note: Please use white backgrounds for your presentation.)
Dates
Molecule (Chapter)
Lecturer
January 15 Rapamycin (Chapter 31) Robert Maleczka
January 15
 Keeping up with the literature
 Luis Sanchez
January 29 Erythronolide B (Chapter 11) Damith Perera
January 29
 Methyl Homosecodaphniphyllate (Chapter 26) Hao Li
February 5
 Amphotericin (Chapter 24) Benjamin Weaver
February 5 Ginkolide B (Chapter 25) Rosario Amadosierra
February 12 Asteltoxin (Chapter 20)
 Luis Mori
February 12 Calicheamicin (Chapter 30) Salinda Wijeratne
March 5 Hirsutene  (Chapter 23) Beth Schoen
March 5 Progesterone (Chapter 6) Gregory Spahlinger
March 19
 Periplanone B (Chapter 13) Nastaran Salehimarzijarani
March 19
 Endiandric Acids A–D (Chapter 17) Jason Clasper
March 26
 Zaragozic Acid (Chapter 35) Fangyi Shen
March 26
 Strychnine (Chapter 33) Peter Heisler

(Clicking on the molecule's name will down load that student's presentation as a pdf file)

Total Synthesis (100 pts):

In March, each of you will be given a natural product for which you are to design a synthesis.  We will first meet on April 16th at which time you should plan on presenting a 10 minute retrosynthesis of your molecule highlighting what you view will be the key points of your proposed synthesis.  I will expect a hard copies your retrosyntheses at this time.  On April 25 we will meet for your full 30 minute (maximum!) presentation.  You should bring handouts of your presentation for the entire audience.

A written report describing your synthesis is also part of this assignment.  This report should resemble a grant proposal (or journal manuscript) with a strict 10-page limit, including all Schemes but excluding references.  Your written report is also due on April 25th.  Each synthesis will be graded on the basis of your presentation, how you respond to questions, chemical soundness, creativity, thoroughness, the clarity of your final report, and your attendance.  More details on this assignment will be given later in the semester.

Total Synthesis Schedule:

First Oral Report (10 pts):  To be presented Saturday April 16 starting at 9 am in room 581E.

Written Report: (40 pts):  ALL reports are due 7 pm Monday April 25.

Final Oral Report (50 pts):  Monday April 26, 6 pm, room 581W.

Grading Scheme:

Two examinations = 200 points
Classic Synthesis Presentation = 50 points
Total Synthesis First Oral Report = 10 points
Total Synthesis Final Oral = 50 points
Total Synthesis Written Report = 40 points
Final examination = 150 points
Total = 600 points

Missed Exams and assignments:

No makeup exams will be given. If you miss an hourly examination due to religious holidays, unavoidable personal commitments, illness, etc., your course grade will be calculated by adding the point value (100 pts) of each missed exam to the Final Exam.*

Likewise, if you miss your "Classic Synthesis" presentation, we will pro-rate your the final exam.*

           *If you know you will have a conflict with the dates indicated above AND you let me know by January 19th I will arrange for a makeup date.)

Homework:

Homework will be assigned periodically, but will not be considered directly in the grading of the course.

Supplemental Material:

Old exams are available. You may also find Professor Reusch's Virtual Textbook of Organic Chemistry helpfull. Furthermore, please check the "announcements" link on the 852 web page frequently as important information, course up-dates, and additional materials will be placed there as the course progresses.

Class Conduct:

Professional, courteous, and ethical conduct is expected of all students at all times.  Likewise, diversity among students should be respected.  Finally, please turn off your cell phones before entering the class room.

Policy on Cheating:

In order to discourage cheating, the instructor may make copies of some pages of some exams. Any student caught cheating will receive a grade of 0.0 for that test. In addition, a letter describing the incident will be sent to the chairperson of the Chemistry department, as well as that student's Department Chair, College Dean, and each memeber of the student's Ph.D. committee.