2018 Advanced Organic Synthesis I

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Graduate major in Chemical Science and Engineering
Ito Shigekazu 
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Course description and aims

[Summary of the lecture] In this lecture, chemistry of heterocyclic compounds, especially natural alkaloids, is overviewed, and cyclization reactions and property of the heterocyclic compounds are explained. Also aromaticity and the related functionality are discussed.
Advanced Organic Synthesis II is subsequently opened after this course.
[Aim of the lecture] Heterocyclic structures are included in many drugs, agricultural chemicals, and electro-functional materials. In this lecture, heterocyclic chemistry that is prerequisite to researchers based on organic chemistry will be overviewed. Students will understand the fundamentals of synthesis and properties of heterocyclic compounds.

Student learning outcomes

By the end of this course, students acquire the following ability:
(1) Overview chemistry of heterocyclic compounds.
(2) Explain properties of the heterocyclic compounds in nature.
(3) Explain methods of construction, fundamental properties, and functionality of heterocyclic compounds.


heterocycles, alkaloids, cyclizations, aldol reactions, catalytic reactions, cycloadditions, electron-deficient, electron-excessive, aromaticity

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) overview of heterocyclic compounds, (2) synthetic methods for the cyclic structures, and (3) structure and properties of heterocycles. 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 Overview of heterocyclic chemistry Explain overview heterocyclic chemistry.
Class 2 Heterocycles in nature Explain natural heterocyclic compounds.
Class 3 Intramolecular cyclizations 1: Paal-Knorr methods Explain Paal-Knorr methods.
Class 4 Intramolecular cyclizations 1: Catalytic methods Explain catalytic synthesis of heterocycles.
Class 5 Cycloadditions Explain cycloadditions affording heterocycles.
Class 6 Chemistry of electron-deficient heterocyclic compounds Explain chemistry of electron-deficient heterocyclic compounds.
Class 7 Chemistry of electron-excessive heterocyclic compounds Explain chemistry of electron-excessive heterocyclic compounds.
Class 8 Practice problems and interpretation for confirming the level of understanding Solve practice problems by accurate understanding of the above all lectures.


None required.

Reference books, course materials, etc.

1) L. D. Quin, "Fundamentals of Heterocyclic Chemistry" ISBN-13: 978-047056695
S. Funayama, "Alkaloids: Doku to Kusuri no Houko (in Japanese)" ISBN-13: 978-4320055049
2) Materials used in class can be found on OCW-i.

Assessment criteria and methods

Practice problems and interpretation for confirming the level of understanding (70%), level of class participation (30%) (The level of class
participation will be calculated by discussion, small examination and so on in the lecture.)

Related courses

  • CAP.A421 : Advanced Design of Organic Reaction Processes I
  • CAP.A422 : Advanced Design of Organic Reaction Processes I
  • CAP.T431 : Advanced Organometallic Chemistry and Catalysis I
  • CAP.T432 : Advanced Organometallic Chemistry and Catalysis II
  • CAP.A521 : Advanced Molecular Design for Organic Synthesis I
  • CAP.A522 : Advanced Molecular Design for Organic Synthesis II

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

The condition of the study will not be made, but enrollment in the related course of organic chemistry is desirable.

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