Topic outline

  • General


    • Learning Goal

      After the course a student is able to design syntheses for complex organic molecules. Students can search literature to support their synthetic planning and are able to present their plans using ChemDraw.

      N.B. The course assumes that you are fully fluent with curved arrow mechanisms and basics of stereochemistry and conformational analysis. If you are unfamiliar with these concepts it's heavily suggested that you take our course Advanced Organic Chemistry first.

      As usual with Juha's courses - the more work you put in the more you learn and memorization is useless. The only way to truly learn fundamental organic chemistry is through hands-on problem solving.

      While learning to solve complex mechanisms is like learning mathematics, learning to design syntheses is like learning art. You need to be creative, perseverant, collaborative, aware of the big picture and draw a lot!

    • Instructor

      • Assistant Professor Juha Siitonen
      • Field of research: Total synthesis of natural products, method development, physical organic chemistry, and theoretical and computational organic chemistry
      • E-mail: juha.siitonen [at] aalto.fi
      • Office: C316

    • Course Material

      Course textbook: Wyatt, Warren, Organic Synthesis - Strategy and Control, 1st edition. Wiley, 2007


      Molecular model kits: HGS Maruzen 1003Alpha molecular model kit →. Available on Amazon and provided by Juha's group in the problem sets and synthesis clinics.

      Software: ChemDraw installed on your desktop computer. Available to download via Perkin Elmer online→

      Software: Reaxys database. Available on Aalto network on via VPN at www.reaxys.com→

      For those really interested in organic synthesis, also consider:

    • Course Structure

      The course consists of the following elements:
      • Lectures - covering the basic theoretical frameworks with hands-on problem solving
      • Discussions - hands-on problem solving with problem sets (PS1–4)
      • Synthesis clinics - sessions for getting help with brainstorming your syntheses
      • Synthesis plan presentations (20 points)
      • Homework problems (20 points)

      You will get actual hands-on experience on designing a total synthesis for a complex natural product in pairs. Your synthetic plan will be presented to the rest of the class and you will get feedback on your synthetic approach.


    • Course schedule

      Week                
      		Lecture (Wednesday/Tuesday)
      		 Discussion (Friday)
      		 Homework
      1 (10.1. →)
      		 Purpose of synthesis, retrosynthetic thinking, target analysis, simplification, strategic bond indentification
      		 PS1
      2 (17.1. →)
      		 C–C bond making reactions: Advanced enolates, acyclic stereocontrol ChemDraw/Reaxys
      3 (24.1. →)
      		 C–C bond making reactions: Organometallics, Pd-cross coupling Synthesis clinic 1
      		 HW1 (26.1)
      4 (31.1. →)
      		 C=C bond making reactions: Wittig, hydrogenation, Julia eg. Presentation 1 (2.2.)
      5 (7.2. →)
      		 C=C functionalization methods: dihydroxylation, epoxidation, ozonolysis etc.
      		 PS3
      6 (14.2. →)
      		 Stereocontrol, setting absolute configuration
      		 Synthesis clinic 2
      		 HW2 (16.2.)
      7
      		Exam week, no classes
      		 Exam week, no classes
      8 (27.2. →)
      		 Functional group interconversions: Redox manipulations, substitutions  PS4   
      9 (5.3. →)
      		 Challenging transformations: Rearrangements, domino reactions, fragmentations
      		 Synthesis clinic 3
      10 (12.3. →)
      		 Implementing strategies, case studies
      		 Presentation 2 (15.3.)
      		  

    • Grading

      The total number of points that you can acquire is 40 and it comprises of the following:
      • Homework problems 2×10 p = 20 p
      • Synthesis plan 20 p
      In addition you can aquire bonus points from more challenging problems embedded into the homework problems.

      Grade

      Points

      F

      0–20

      1

      20–24

      2

      24–28

      3

      28–32

      4

      32–36

      5

      36–40

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