2017 Advanced Organic Chemistry IV (Organic Synthesis)

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Undergraduate major in Chemical Science and Engineering
Mikami Koichi 
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Course description and aims

[Summary of the lecture] In this lecture, carbon skeletons of organic compounds will be focused in view of their variations. Characteristics of functional groups will also be taught. The synthetic methods for the construction of carbon skeletons will be emphasized as the key in organic synthesis.
[Aim of the lecture] Students understand the mechanism for stereoselective organic reactions and the reported synthesis of complex organic compounds, such as natural products. Students acquire the ability to propose the synthetic plan for the synthesis of complex organic molecules.

Student learning outcomes

By the end of this course, students acquire the following ability:
(1) Explain characteristic features of functional groups, which are necessary for drawing up the synthetic plan.
(2) Explain the mechanism and origin for chemoselectivity, regioselectivity, and stereoselectivity of the reactions.
(3) Draw up the multi-step synthetic plan of the complex organic compounds.


Synthesis, retro-synthesis, CCF, FGI, FGT, stereoselectivity, chemoselectivity, regioselectivity, common atoms, linear/convergent syntheses, symmetry, key itermediates

Competencies that will be developed

Specialist skills Intercultural skills Communication skills Critical thinking skills Practical and/or problem-solving skills

Class flow

This lecture will proceed in the following order: (1) synthesis, retro-synthesis, (2) CCF (Carbon-Carbon Bond Formation), FGI (Functional Group Interconversion), FGT (Functional Group Transposition), selectivity, (3) linear/convergent syntheses, symmetry of target molecules, synthetic itermediate and common atom. In the last day, practice problems and interpretation of them will be carried out to confirm the level of understanding.

Course schedule/Required learning

  Course schedule Required learning
Class 1 Introduction Explain the importance of organic syntheses.
Class 2 Complexity in carbon skeletons in target molecules Analyze complexity in carbon skeletons.
Class 3 Characteristic functional groups and chemoselectivity thereof Explain characteristics in functional groups and chemoselectivities.
Class 4 CCF: Carbon-Carbon Bond Formation Explain synthesis of carbon skeletons.
Class 5 Stereoselectivity: origin and control Explain origins and control of stereoselectivity.
Class 6 Synthesis and retro-synthesis of longifolene Explain (retro) syntheses of fused ring systems.
Class 7 Multi-step syntheses Draw up the multi-step synthetic plan of the target compound.
Class 8 Practice problems and interpretation for confirming the level of understanding Discuss the reaction mechanism and draw up the synthetic plan of the target molecules.


R .E. Ireland「Organic Synthesis」

Reference books, course materials, etc.

S. Warren「Designing Organic Synthesis」ISBN4-06-139317-0

Assessment criteria and methods

Practice problems and interpretation for confirming the level of understanding (85%), level of class participation (15%) (The level of class
participation will be calculated by discussion, small examination and so on in the lecture.)

Related courses

  • CAP.B211 : Organic Chemistry I (Alkanes) (Chemical Science and Engineering)
  • CAP.B212 : Organic Chemistry II (Alkenes)
  • CAP.B213 : Organic Chemistry III (Aromatic Compounds)
  • CAP.B214 : Organic Chemistry IV (Nucleophilic Substitution)

Prerequisites (i.e., required knowledge, skills, courses, etc.)

The condition of the study will not be made, but it is desirable to study Organic Chemistry I (Alkanes) (Chemical Science and Engineering),
Organic Chemistry II (Alkenes), Organic Chemistry III (Aromatic Compounds), and Organic Chemistry IV (nucleophilic substitution).

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