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Syllabus for Chemistry 852 - Spring 2017 (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 8:309:50 am, room 111 Biochemistry Building
                               Class Presentations: Saturdays 10 am - 12 pm, room 481E Chemistry Building

Course Website:   


Professor Robert E. Maleczka, Jr.  
phone: 353-0834
office hours: by appointment (485B Chemistry)

Course Coordinator:

Ms. Nancy Lavrik

Required Text:

        Paul Wyatt & Stuart Warren, Organic Synthesis: Strategy and Control, Wiley, 2007.  ISBN-978-0-471-92963-5

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

Planned Lecture Schedule*
Wyatt/Warren Reading Assignments
January 10
Course Intro/Review of Physical Data -
January 12 Introduction to Retrosynthetic Analysis
Chapter 1
January 18* Chemoselectivity Chapter 2
January 19 Overview of Aldol Reactions Chapter 3
January 21** Regioselectivity: Controlled Aldol Reactions Chapter 3
January 26 Stereoselectivity: Stereoselective Aldol Reactions Chapter 5
January 31 Alternative Strategies for Enone Synthesis Chapter 5
February 1* The Synthesis of Cyclopentenones Chapter 6
February 7
The Ortho Strategy for Aromatic Compounds Chapter 7
February 9
σ-Complexes of Metals Chapter 8
Sat. Feb. 11 (9 am noon) Exam 1 to be held in room 126 100 pts
February 14
Controlling the Michael Reaction Chapter 9
February 16
Specific Enol Equivalents Chapter 10
February 21 Extended Enolates
Chapter 11
February 23 Allyl Anions
Chapter 12
February 28
Homoenolates Chapter 13
March 2
Acyl Anion Equivalents Chapter 14
March 14 Synthesis of Double Bonds of Defined Stereochemistry
Chapter 15
March 16
Stereocontrolled Vinyl Anion Equivalents Chapter 16
March 21
Electrophilic Attack on Alkenes Chapter 17
March 23
Palladium-Catalyzed CC Coupling Chapter 18
Sat. March 25 (9 noon)
Exam 2 to be held in room 126
100 pts
March 28
Palladium-Catalyzed CC Coupling Chapter 18
March 30 Allylic AlcoholsAllyl Cation Equivalents (and More) Chapter 19
April 5*
Controlling of Stereochemistry - Introduction Chapter 22
April 6
Controlling Relative Stereochemistry Chapter 21
April 11
Asymmetric Induction: Reagent-Based Strategy Chapter 24
April 13
Asymmetric Catalysis: Formation of CO and CN Bonds Chapter 25
April 18
Asymmetric Catalysis: Formation of CH and CC Bonds Chapter 26
April 20
Asymmetric Induction: Substrate-Based Strategy Chapter 27
April 25
Kinetic Resolution Chapter 28
April 27
Enzymes: Biological Methods in Asymmetric Synthesis Chapter 29
Wed. May 3 (8 am noon) All inclusive Final Exam to be held in room 126 150 pts

*These lectures will be held Wednesday evening at 7 pm in room 581W.

**These lectures will be held Saturday following the Classic talks in room 481E.

Note: 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".  The presentations will begin at 10 am and take place in room 481E.  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.)
Molecule (Chapter)
January 21 Rapamycin (Chapter 31) Robert Maleczka
January 28 Strychnine (Chapter 2)   Kio Tanemura 
January 28 Methyl Homosecodaphniphyllate (Chapter 26)   Yuting Zhou
February 25 Erythronolide (Chapter 11)   Ryan Fornwald
February 25 Asteltoxin (Chapter 20)   Monique Noel  
February 25 Monensin (Chapter 12)   Zibin Tan
March 4 Monensin (Chapter 15)   Katarina Keel
March 4
Amphotericin (Chapter 24)   Dhwani Kansal
March 4
Zaragozic Acid (Chapter 35)   Soham Maity
March 11 Cytovaricin (Chapter 28)
  Seokjoo Lee
March 11 Taxol (Chapter 34)   Jose Montero
March 11 Periplanone B (Chapter 13)   Md Shafaat Al Mehedi
April 8
Endiandric Acids AD (Chapter 17)   Mengxia Sun
April 8 Hirsutene  (Chapter 23)   Mehdi Moemeni

(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 at 6 pm on Monday April 17 in room 581W.  At that meeting you will be expected to present a 10 minute retrosynthesis of your molecule highlighting what you view will be the key points of your proposed synthesis, including the means by which your synthesis will be made asymmetric.  I will expect a hard copies your retrosyntheses at this time.  On the evenings of April 27 & 28 we will meet at 6 pm in room 581W for a full presentation of your synthesis (30 minutes maximum!).  Again you need to bring me a hard copy of your presentation.

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 at 6 pm on April 26th.  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 Monday April 17 starting at 6 pm in room 581W.

Written Report: (40 pts):  ALL reports are due at 6 pm Thursday April 27th (2nd drafts handed in after 4/27 will NOT be graded).

Final Oral Report (50 pts):   To be presented over two evenings:  Thursday April 27 and Friday April 28, starting at 6 pm each night (581W).  The presentation order will be determined at random, so everybody needs to be prepared to present at 6 pm 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 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 21 I will arrange for a makeup date.)


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 helpful. 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 classroom.

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.