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Course code:
255H1

Course name:
Synthesis of Complex Organic Molecules

Academic year:

2017/2018.

Attendance prerequisites:

No prerequisites.

ECTS:

9

Study level:

graduate academic studies, integrated basic and graduate studies

Study programmes:

Chemical Education: 5. year, winter semester, elective (E5AP1) course

Chemistry: 1. year, winter semester, elective (E51H1) course

Teacher:

Radomir N. Saiшiц, Ph.D.
full professor, Faculty of Chemistry, Studentski trg 12-16, Beograd

Assistant:

MiloЙ D. Trajkoviц, Ph.D.
assistant, Faculty of Chemistry, Studentski trg 12-16, Beograd

Number of hours:

Weekly: four hours of lectures + two hours of exercises + three hours of labwork (4+2+3)

Study purpose:

The course entitled Synthesis of Complex Organic Molecules enables students to accomplish independently the retrosynthetic analysis of moderately complex molecules (synthetic strategy), as well as to plan and realize the sequence of reactions that would put this retrosynthetic conception into synthetic practice (tactics of synthesis). Given the fact that stereochemical aspect of organic molecules greatly contributes to molecular complexity, in the first part of the course, students are acquainted with the most important reactions of carbon-carbon and carbon-heteroatom bond formation which allow for the control of the relative and absolute configuration at the newly-created stereocenters. The second part of the course deals with systematic retrosynthetic analysis of target molecules. This part of the course is interactive and encompasses the case studies, with active participation of students. Through the discussions of proposed solutions to synthetic problems, criteria are established for the choice and evaluation of retrosynthetic pathways. During labworks students independently realize the syntheses of selected compounds, using modern reactions, recently described in the literature. The main goal is to enable student to independently plan and realize the syntheses of complex molecules, which involves: 1) mastering the principles of retrosynthetic analysis; 2) understanding the principles of asymmetric synthesis; 3) application of functional groups protection/deprotection.

Study outcome:

The knowledge acquired during this course should allow student to successfully participate to the research, or production, activities in the fields of medicinal chemistry, chemical biology, pharmaceutical chemistry, new materials etc.

Coursework methods:

Lectures, seminars, labworks.

Extracurricular activities:

Literature:

Core literature:

  • E. J. Corey, X.-M. Cheng: The Logic of Chemical Synthesis, J. Wiley, 1989.
  • S. Warren: Organic Synthesis: The Disconnection Approach, J. Wiley & Sons, 1985, N. Y.
  • Р. Н. Саичић: Синтезе комплексних органских молекула - скрипта, 2007.

Additional literature:

  • M. Smith: Organic Synthesis, McGraw-Hill, 2002.
  • F. A. Carey, R. J. Sundberg: Advanced Organic Chemistry, 4th edition, Parts A (ISBN: 0-306-46245-1) and B (ISBN: 0-306-46242-7), Kluwer Academic/Plenum Publishers, N. Y. 2001.
  • Примарна литература доступна у библиотеци Хемијског факултета, као и у електронском облику
  • Organic Synthesis, Collective volumes 1-9
  • Encyclopedia of Reagents for Organic Synthesis, Ed. L. A. Paquette, J. Wiley, 1996.

Additional materials:

Course activities and method of grade assignment

Lectures:

20 points (4 hours weekly)

Programme:

  • Introductory lecture
  • Aldol reactions of the I and II group enolates;
  • Aldol reaction of boron enolates;
  • Mukaiyama reaction;
  • Claisen and Cope rearrangements;
  • Sharpless asymmetric epoxydation, dihydroxylation and amminohydroxylation;
  • Baeyer-Villiger reaction;
  • Protective groups in organic synthesis;
  • Retrosynthetic analysis of organic molecules (1): Elements of molecular complexity. Associative-inductive and logical-systematic approach to organic synthesis;
  • Retrosynthetic analysis of organic molecules (2): A synthon. Application of the synthon approach in retrosynthetic analysis;
  • Retrosynthetic analysis of organic molecules (3): Retron and transform. Classification of transforms and their application in retrosynthetic analysis;
  • Retrosynthetic analysis of organic molecules (4): Analysis of topologically complex systems;
  • Retrosynthetic analysis of organic molecules (5): Analysis of stereochemically complex systems;
  • Retrosynthetic analysis of organic molecules (6): Functional groups as guiding elements for retrosynthetic analysis. Symmetry of organic molecules and bidirectional analysis;
  • Retrosynthetic analysis of organic molecules (7): Closing lecture. Concluding remarks and selected examples of total syntheses.

Exercises:

0 points (2 hours weekly)

Labwork:

10 points (3 hours weekly)

Semester papers:

10 points

Oral exam:

60 points

Wed Oct 4 11:07:36 2017

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