Design Molecular

Objectives

The UC aims to provide the students with an understanding of the basic concepts and methodologies underlying the rational design and synthesis of new compounds in the laboratory and in industry. Upon completion of the course, the students are expected to: - Be familiar with the use of retrosynthetic analysis tools, functional group interconversion, and selective protection/deprotection of reactive groups. - Identify and compare the advantages and disadvantages of different synthetic methodologies toward the same target molecule, both on a lab scale and under scale-up conditions. - Find relevant literature to support the selection of a given synthetic strategy by browsing adequate databases. - Present and discuss in a critical manner recent work on synthetic methodologies. - Analyze, plan, and carry out the synthesis of target molecules using multistep modern methodologies. - Understand and discuss the mechanistic aspects of the reactions involved.

Syllabus

Principles of retrosynthetic analysis; disconnections and synthons. Catalytic and stoichiometric methods for functional group interconversion. Strategies of reactive group protection/deprotection. Selectivity and reactivity of specific reagents and functional groups. Modern methods for C-C and C-heteroatom bond formation, with emphasis on catalytic methodologies. Principles of asymmetric synthesis - the chiral pool, building block synthesis with chiral reagents, chiral auxiliaries and chiral catalysis; organocatalyis and biocatalysis. ‘Green’ synthetic approaches to relevant target molecules. Common synthetic procedures in the pharmaceutical and food industries.

Cross Competence Component

The course has a strong project component, involving literature search, critical selection of adequate synthetic conditions for a target molecule and the conduction of the selected laboratory sequence. This requires autonomy, critical thinking, development of arguing skills and teamwork. Additionally, the TP sessions provide a forum for presenting and debating case studies comparing advantages and disadvantages of different synthetic methodologies for the same target molecule.

Laboratorial Component

At the start of the course, groups of 2 students will each be assigned a feasible synthetic project. Each group is expected to search the literature for possible synthetic approaches to obtain the target molecule, discuss their relative merits, select a sequence of synthetic steps and experimental conditions, conduct the synthesis, and use spectroscopic characterization methods (e.g., IR, NMR, MS, X-ray, whenever appropriate) to assess the identity and purity of the relevant synthetic intermediates and the target molecule.

Programming And Computing Component

The students will make ample use of database search. The use of open-source computer-assisted organic synthesis software is also contemplated.

Ethical Principles

All members of a group are responsible for the group´s work. In any assessment, every student shall honestly disclose any help received and sources used. In an oral assessment, every student shall be able to present and answer questions about the entire assignment and solution.