MSU CNS Logo. Click here to go to the CNS home page.MSU Logo. Click here to go to the MSU home page.

MSU Chemistry Logo. Click here to go to the Chemistry home page.

Syllabus for Chemistry 852 - Spring 2009 (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 136 Chemistry Building
                               Class Presentations: Saturdays 9-11 am, room 136 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)

TA:

Mr. Luis Sanchez
email: sanchez@chemistry.msu.edu 
office hours: by appointment (503 Chemistry)

Course Secretary:

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


Required Texts:

1.  F. Carey & R. Sundberg, Advanced Organic Chemistry: Part A: Structure and Mechanism (5th ed), Springer, 2007.  ISBN-978-0-387-44897-8
2.  F. Carey & R. Sundberg, Advanced Organic Chemistry: Part B: Reaction and Synthesis (5th ed), Springer, 2007.  ISBN-978-0-387-68354-6


Recommended Text: K.C. Nicolaou & E.J. Sorensen, Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996.  ISBN-3-527-29231-4


Dates
Planned Lecture Schedule*
Carey Chapters (vol. B)
Jan. 13
 Course Intro/General Principles CEM 850
January 15–27 Chemistry of Unactivated Alkenes & Alkynes 4th Ed: 4, 9.1, 11, vol. A: 5–6
Jan. 29 – Feb. 5
 Aromatic Substitution 4th Ed: 11
February 10–19
 Oxidations and Reductions 4th Ed: 12 & 5
Sat. Feb. 21 (9 – noon)
Exam 1 to be held in room 281
100 pts
Feb. 24 – March 3
 Nucleophilic Carbon Reagents Part I: Grignards, Wittigs, etc. 4th Ed: 2.4-2.6, 7, 8.1
March 5–24
  Nucleophilic Carbon Reagents Part II:  Enolates and Related Nucleophiles 4th Ed: 1, 2, vol. A 7
March 26–31
 Nucleophilic Carbon Reagents Part III: Allylations, Crotylations, etc.
 4th Ed: 9.1-9.3
Sat. April 4 (9 – 11 am)
Exam 2 to be held in room 110
100 pts
April 2–9
 Sigmatropic Reactions 4th Ed: 6
April 14–21  Cycloadditions & Cationic Cyclizations
 4th Ed: 6 & 10
April 23–30
 Transition Metal-Mediated and Related Reactions
 4th Ed: 8.2-8.5, 10.2-10.3
Tuesday May 5
(7:45–10:45 a.m.)		 Final Exam room TBA 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 On most Saturdays one or two students will each present a synthesis from Nicolaou's "Classics in Total Synthesis" (on reserve in the BPS library).  The presentations will begin at 9 am and take place in room 136.  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
Jan. 17
 Rapamycin (Chapter 31) Robert Maleczka
Jan. 31
 Strychnine (Chapter 2) Kumar Ashtekar
Jan. 31 Erythronolide B (Chapter 11) Tetyana Berbasova
Feb. 7
 Amphotericin (Chapter 24) Philipp Roosen
Feb. 7
 Zaragozic Acid (Chapter 35) Steven Dulaney
Feb. 14 Cytovaricin (Chapter 28) Yiding Ma
Feb. 14 Palytoxin (Chapter 36)
 Wen Yuan
March 7
 Endiandric Acids A–D (Chapter 17) Luis Sanchez
March 7 Methyl Homosecodaphniphyllate (Chapter 26) Hao Li
March 14
 Asteltoxin (Chapter 20) Luis Sanchez
March 14
 Hirsutene (Chapter 23)
 Heyi Hu
March 21 Brevetoxin (Chapter 37) Amila Dissanayake
March 21
 Progesterone (Chapter 6) Philip Bentley
March 28 Ginkolide B (Chapter 25) Rosario Amadosierra
March 28 Prostaglandin F2a (Chapter 5) Quanxuan Zhang
March 28
 Strychnine (Chapter 33) Nicole Hewlett

(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 18th 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 everyone’s retrosyntheses at this time.  Then on April 27, 28, and 29 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.  Even if your oral presentation is on the 28th or 29th, a detailed written report on your synthetic plan will be due April 27th.  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 with be given later in the semester.

Total Synthesis Schedule:

First Oral Report (10 pts): To be presented Saturday April 18 starting at 9 pm in room 136.

Written Report: (40 pts): ALL reports are due 7 pm Monday April 27 (2nd drafts handed in after 4/27 will NOT be graded).

Final Oral Report (50 pts): To be presented over three days:  Monday April 27, Tuesday April 27, and Wednesday April 29.  Tentatively, all presentations will take place in room 136.  The presentation order will be determined at random, so everybody needs to be prepared to present on April 27th.

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:

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 oral presentation on your total synthesis.

Problem Sets:

Problem sets will be assigned. These will be handed in and corrected; however the scores 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 as well as an excellent collection of lecture notes assembled by Prof. D. Evans and colleagues at Harvard University 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.

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.