Synthesis of Complex Organic Molecules   (255H2)

Academic year:

2023/2024.

Attendance requirements:

There are no requirements.

ECTS:

9

Study level:

Study programs:

Teacher:

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

Assistant:

Bojan Z. Vulović, Ph.D.
assistant professor, Faculty of Chemistry, Studentski trg 12-16, Beograd

Hours of instruction:

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

Goals:

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.

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.

Teaching methods:

Lectures, seminars, labworks.

Extracurricular activities:

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Coursebooks:

Main coursebooks:

• 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.
• Ŕ. ˝. ÁĐŘçŘű: ÁŘÝâŐ×Ő ÚŢÜßŰŐÚáÝŘĺ ŢŕÓĐÝáÚŘĺ ÜŢŰŐÚăŰĐ - áÚŕŘßâĐ, 2007.

Supplementary coursebooks:

• 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.
• żŕŘÜĐŕÝĐ ŰŘâŐŕĐâăŕĐ ÔŢáâăßÝĐ ă ŃŘŃŰŘŢâŐćŘ ĹŐÜŘřáÚŢÓ äĐÚăŰâŐâĐ, ÚĐŢ Ř ă ŐŰŐÚâŕŢÝáÚŢÜ ŢŃŰŘÚă
• Organic Synthesis, Collective volumes 1-9
• Encyclopedia of Reagents for Organic Synthesis, Ed. L. A. Paquette, J. Wiley, 1996.

Additional material:

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Lectures:

20 points (4 hours a week)

Syllabus:

• 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 a week)

Labwork:

10 points (3 hours a week)

Semester papers:

10 points

Oral exam:

60 points