1. Your undergraduate organic text.
2.
George S. Zweifel,
Michael H. Nantz, and Peter Somfai, Modern
Organic
Synthesis: An Introduction, 2017, Wiley. ISBN-978-1-119-08653-6.
3. Paul
Wyatt & Stuart Warren, Organic
Synthesis:
Strategy and Control, Wiley, 2007. ISBN-978-0-470-92963-5.
4. K. C. Nicolaou & E. J. Sorensen, Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996. ISBN-3-527-29231-4. (On reserve in the MSU library)
5. The ACS Organic Division
recently released a new resource for organic
chemists: https://organicchemistrydata.org/.
The
Reich
Collection of Resources includes ~700 Total Syntheses searchable
and categorized by compound name, named reactions used,
chemoselectivity, rings formed, reaction types, and reagents
used, etc.; a comprehensive Topics in NMR database,
and information on pKa tables, electron pushing, A-values, nomenclature, organometallic chemistry,
etc.
Announcements: Here you will find
important information, course up-dates, and additional
materials. Please check frequently as items will be placed
there as the course progresses.
|
|
|
January 10 |
Course Intro | |
January 12 |
Rapamycin & Methyl Homosecodaphniphyllate | Nicolaou & Sorensen |
January 14–31 | Classics in Total Synthesis | Nicolaou & Sorensen |
February 2 |
Synthetic
Design |
Zweifel/Nance
Chapter 1 |
February 4, 7 |
Conformational Analysis |
Zweifel/Nance
Chapter 2 |
February 9, 11 |
Protective
Groups / Chemoselectivity |
Zweifel/Nance Chapter 3 |
February 14 (am), 16, 18 |
Oxidations
and Reductions |
Zweifel/Nance Chapter 4 |
Feb. 21 (6:00 – 9:00 pm) | Exam 1 to be held in room 127 | 100 pts |
February 23, 25, 28, March 2 |
Reactions of C–C pi-Bonds | Zweifel/Nance Chapter 5 |
March 4, 14 |
Formation of C–C pi-Bonds | Zweifel/Nance Chapter 7 |
March 16, 18, 21 | Formation of C–C bonds via Enolate Anions | Zweifel/Nance Chapter 6 |
March 23, 25 | Formation of C–C bonds via Organometallics | Zweifel/Nance Chapter 7 |
March 28 (6:00 – 9:00 pm) |
|
100 pts |
March 30–April 1 | Pericyclic Reactions | Zweifel/Nance Chapter 9 |
April 4, 6 |
Asymmetric
Catalysis |
Warren Chapter 25, 26 |
April 8 |
Organocatalysis | Warren Chapter 28, 29 |
April 11 (am), 13, 15 | Aromatic Substitution / CH activation | Warren Chapters 7, 33 |
April 11 (pm) | Synthesis Presentations I | 10 pts |
April 18, 20, 22 | Reactive Intermediates | Zweifel/Nance Chapter 9 |
April 25, 27, 29 |
Heterocycles |
Warren Chapters 32, 34, 35 |
April 25 |
Written Reports Due, 6 pm, Room TBD | 40 pts |
April 25, 26, 27 | Synthesis Presentations II, 6 pm, Room TBD | 50 pts |
Tues. May 3 (Time TBD) | All inclusive Final Exam to be held in room TBD | 150 pts |
*Subject to Change.
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):
|
|
|
January 12 | Rapamycin (Chapter 31) | Robert Maleczka |
January 12 | Methyl Homosecodaphniphyllate (Chapter 26) | Robert Maleczka |
January 14 | Erythronolide B (Chapter 11) | Nick Wills |
January 14 | Reserpene (Chapter 4) | Nikita |
January 19 | Strychnine (Chapter 2) | Sodiq Nafiu |
January 19 | Strychnine (Chapter 33) | Nathan Slater |
January 21 |
Monensin (Chapter 12) | Hanin Sarhan |
January 21 |
Monensin (Chapter 15) | Vindula Alwis |
January 24 | Periplanone (Chapter 13) | Sonam Shivtarkar |
January 24 | Periplanone (Chapter 21) | Nethma Wethalawe |
January 26 | Progesterone (Chapter 6) | Rosemary Augustine |
January 26 | Endiandric Acids A–D (Chapter 17) | Shannon Cartwright |
January 28 | Amphotericin B (Chapter 24) | Bahareh Ghaffari |
January 28 | Zaragozic Acid (Chapter 35) | Sydney Cobb |
January 31 (am) | Indolizomycin (Chapter 27) | Keyvan Pedrood |
January 31 (am) | Indolizomycin (Chapter 27) | Keshav Prahaladi |
January 31 (pm) | Asteltoxin (Chapter 20) | Milad Pedarpourvajargahy |
January 31 (pm) | Hirsutene (Chapter 23) | Salma Begum |
|
|
Total Synthesis (100 pts):
In early March, each of you will be given a natural product for which you are to design a synthesis. We will first meet on at 7 pm on Monday April 11. At that meeting, you are to present a retrosynthesis (10-minutes max!) 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. An electronic copy of your retrosynthesis is due at 7 pm that day. A written report describing your synthesis is part of this assignment. This report should resemble a second-year oral exam written report with a ≤4000-word limit, not counting Scheme captions and references (no limit on the number of Schemes). An electronic of your written report is due at 6 pm on April 25. On the evenings of April 25–27 we will meet at 6 pm (room TBD) for a full presentation of your synthesis (30 minutes maximum!) . 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): Presented April 11 starting
at 6 pm.
Written Report: (40 pts): An electronic copy is due at 6 pm Monday April 11
Final Oral Report (50 pts): Presented over three evenings Monday April 25,
Tuesday April 26, and Wednesday April 27, starting at 6 pm each
night. These
meetings are tentatively scheduled to take place in-person in
room 136 (subject to change).
Electronic copies (PDF) of all presentations are due at
6 pm on April 25. Those
giving their oral report on April 26 or 27 are not to present an
edited version of what was handed in on April 25. Doing so will result
in a 0 for the assignment.
Grading Scheme:
Grade
Scale (I reserve the right to adjust this scale downward):
Grade
pts
4.0
>400
3.5
300–400
3.0
200–299
2.5
150–199
Homework: Homework may 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.
COVID-19 Information: The novel coronavirus, which causes
the disease COVID-19, has been declared a worldwide pandemic. The COVID-19 virus is extremely
contagious and is believed to spread mainly from
person-to-person contact. The COVID-19 pandemic represents an
unprecedented public health crisis that has impacted every facet
of life, including the classroom environment. The most up to date
information from MSU is available at: https://msu.edu/together-we-will/covid19-guidance/.
Instructional format: In response to omicron,
instruction will be by zoom throughout the month of January. Come
February, significant
changes in how we conduct in-person classes may be on the
horizon. Should
in classroom attendance be impacted by COVID-19, modifications
may be made to the class format and/or instructor. Similarly, were MSU to
halt in-person graduate study modifications will be made to the
class format.
Face coverings: Face coverings must be worn by
everyone (including all faculty, staff, students, vendors,
and visitors) indoors while on property owned or governed by MSU
and while participating in MSU-related or MSU-sponsored
activities. Thus,
unless you have a University issued exemption, you must wear a
face covering in class. This face covering must cover your
mouth and nose.
Physical distancing: As best as our room assignment
allows, we will be practicing physical distancing in the
classroom. Thus, all students should attempt to
maintain at least six feet distance between themselves and
others (excluding those with whom they live). This applies to all
aspects of the classroom setting, including seating
arrangements, informal conversations, and dialogue between
faculty and students.
Exposure
to COVID-19:
If a student is
exposed to someone who is ill or has tested positive for the
COVID-19 virus, they will stay home and follow MSU guidelines
(see below) to determine what steps should be taken. Students
who miss assignments or exams will have their final pro-rated. Cases of extended
absence will be handled on an individual basis
Self-Monitoring:
Students will self-monitor for flu-like symptoms (for
example, cough, shortness of breath, difficulty breathing,
fever, sore throat or loss of taste or smell). If a student
experiences any flu-like symptoms, they will stay home and
follow MSU guidelines (see below) to determine what steps should
be taken.
Personal
Hygiene. All
students
must maintain proper hygiene and health practices, including:
Adherence
to Signage and Instructions: Students
will (a) look for instructional signs posted by MSU or public
health authorities, (b) observe instructions from MSU or public
health authorities that are emailed to my “msu.edu” account, and
(c) follow those instructions.
Compliance and reporting: Those who come to MSU facilities must
commit to the personal responsibility necessary for us to remain
as safe as possible, including following the specific guidelines
outlined in this syllabus and provided by MSU more broadly (see
below). There may be times when action will be necessary to
reinforce expectations. If
you do not wear appropriate face coverings (see MSU’s
guidelines), do not wear your face covering appropriately
(i.e., over your mouth and nose), or do not adhere to physical
distancing guidelines (i.e., six feet apart), you will be
asked to correct the situation or leave the facility.
In addition, MSU will utilize the processes already in place to
respond to any issues of noncompliance with standards
established for the health and safety of our community. For
classroom disruptions or issues, the responses and processes
that have been used previously remain the first line of action.
If necessary, the student conduct system will be the avenue used
to adjudicate student disciplinary situations.
Additional COVID-19 information. See https://msu.edu/together-we-will/keeping-spartans-safe/
for details about these new policies and procedures and see https://ehs.msu.edu/_assets/docs/fact-sheets/cloth-face-covering-fact-sheet.pdf
for more details about the cloth face coverings guidelines.
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last updated 02/28/2022 by REM