ADVANCED ORGANIC SYNTHESIS

Course objectives

General expected learning outcomes Organic chemistry is a chemistry discipline involving the scientific study of the structure, reactivity, properties and applications of compounds which are formed mainly by carbon atoms, forming covalent bonds, both from natural and artificial sources. The general objective of the SACO course, is to provide students with the knowledge and the competences necessary to understand and apply the key principles of the stereoselective and metal-assisted synthetic routes, touching the main topics studied and acquired during the Organic Chemistry 1 and Organic Chemistry 2 classes. For a CTF student this learning is essential, because most of the synthetic methodology of biologically active compound are based on stereoselective and/or metal-assisted processes. This knowledge will allow the student to be able to understand the new synthetic methodology involved in the construction of biologically active compounds. Furthermore, acquiring of advanced knowledge about organic chemistry will be essential for improving the understanding of the drug-receptor interactions, a crucial topic in different next courses. Specific expected learning outcomes The SACO course is devoted to provide students with the adequate knowledge to be independent in solving problems about specific organic chemistry studies. This ability will be acquired by the means of frontal lesson, submitting to the students illustrative case studies about the synthesis of biologically active compounds. Teaching materials, available on line will support students during the lessons even thought studying the recommended text book is essential to acquire the skills and the competence that are necessary to perform the final exam. In order to improve the exposure ability, students will be constantly encouraged to communicate their ideas to both specialists and non specialists audiences. The Erasmus programme will enable students to improve their communications skills, by exchanging information, problems and solutions. The specific objectives consist in acquiring the following knowledge and expertise: 1) to understand advanced stereochemistry and its importance on the reactivity of organic compounds; 2) to acquire the specific knowledge to understand the main stereoselective reactions; 3) to acquire the specific knowledge to understand the main metal-assisted synthetic procedures; 4) introduction to the bioorganic reaction 5) to acquire the specific knowledge to perform retrosynthetic analysis on molecules of intermediate structural complexity. 7) to acquire the specific knowledge to understand the molecular structure through NMR.

Channel 1
ANTONELLA GOGGIAMANI Lecturers' profile

Program - Frequency - Exams

Course program
Section 1. Stereoselective reactions (16 hours) Stereochemistry and prostereoisomerism. Selectivity in organic chemistry. Kinetic e thermodynamic of the stereoselective reactions. Non linear effects. Diastereoselective reduction of the carbonyl in cyclic and acyclic compounds; Chiral boranes and hydrides. Enolate anion formation: regioselectivity and E/Z ratio. Diastereoselective alkylation of enolate anions. Aldolic reaction . Sharpless oxydation. Fundamentals of organocatalysis. Enantioconvergent reactions. Section 2. Organometallic chemistry (16 hours) Pd(II)-catalyzed reactions of alkenes. Reactions with water, with water and chlorides, with amines, with amides and carboxylic acids. Pd(II)-catalyzed reactions of alkynes. Reactions with amides and amines. Reactions Pd(0)-catalyzed of organic halides and pseudo halides. Reactions with alkenes (Heck reaction), with alkynes, with boronic acids or esters (Suzuki reaction), with nitrogen-containing nucleophiles (Buchwald-Hartwig eaction). Olefin metathesis, Schrock’s catalyst, Grubbs catalyst. Reaction mechanism . RCM, ROM, ADMET, ROMP, CM reactions. Rules for selectivity. Section 3. Bioorganic chemistry (4 hours) Classification of bioorganic reactions. Representative examples. Section 4. Retrosynthesis (4 hours) Disconnections. Retrosynthetic analysis of aromatic compounds. C-X disconnections. Umpolung. Protective group. C-C disconnection. (1,1 C-C, 1,2 C-C, 1,3 C-C, 1,5 C-C). Functional group interconversion (FGI). Section 5. NMR Spectroscopy (8 ore) Introduction to 1D and 2D NMR Spectroscopy; determination of enantiomeric excess via NMR spectroscopy; structural determination of intermediate complexity molecules.
Prerequisites
To fully benefit from the SACO lectures, students should possess the knowledge acquired in the Organic Chemistry I and II courses and Physical Methods in Organic Chemistry. This includes: basic and advanced stereochemistry, reactivity of organic functional groups, main reaction mechanisms, inter- and intramolecular acid and nucleophilic catalysis, and interpretation of 1D-NMR spectra (¹H and ¹³C).
Books
For section 1 and 3: “Advanced Organic Chemistry”; F. A. Carey, R. J. Sundberg, Plenum Publishing Corporation, ISBN 0-306-43457-1. For section 2: “Organometallics in Synthesis”; M. Schlosser, John Wiley & Sons. ISBN 0-471-93637-5; “Palladium Reagents and Catalysts” J. Tsuji. John Wiley & Sons, ISBN 0-470-85033-7. For section 4: “Organic Synthesis: The Disconnection Approach”; S. Warren. John Wiley & Son. ISBN 978-0470712269.
Frequency
Attendance at lectures, although highly beneficial for achieving the learning objectives of the course, is not mandatory.
Exam mode
The final exam can be: a) Traditional, consisting of an oral exam with open-ended questions, which ends with a grade out of thirty; the final grade will take into account the following elements: 1. Knowledge of the entire course material; 2. Ability and clarity in presenting the topics; 3. Ability to connect and synthesize the various topics. b) Preparation and presentation of a brief thesis, on a topic agreed upon with the instructor, related to the subjects covered in the course. The grade out of thirty will reflect: 1. Level of understanding of the topics covered in the thesis that were treated during the course; 2. Clarity in presenting the covered topics. Regardless of the chosen exam format, passing the exam with the minimum grade requires a sufficient understanding of the topics covered in the various parts of the syllabus. To achieve a grade of 30/30 with honors, the student must demonstrate an excellent understanding of all the topics covered during the course, and the ability to logically and coherently connect them. There is no maximum number of exam attempts allowed during the academic year.
Lesson mode
Teaching is delivered in a combined format, both in person and via videoconference. A typical lecture is conducted using course slides, which have been originally prepared by the instructor and are subject to annual revision. The lecture is supplemented with in-depth content presented to students using the electronic whiteboard in the classroom.
ANTONELLA GOGGIAMANI Lecturers' profile

Program - Frequency - Exams

Course program
Section 1. Stereoselective reactions (16 hours) Stereochemistry and prostereoisomerism. Selectivity in organic chemistry. Kinetic e thermodynamic of the stereoselective reactions. Non linear effects. Diastereoselective reduction of the carbonyl in cyclic and acyclic compounds; Chiral boranes and hydrides. Enolate anion formation: regioselectivity and E/Z ratio. Diastereoselective alkylation of enolate anions. Aldolic reaction . Sharpless oxydation. Fundamentals of organocatalysis. Enantioconvergent reactions. Section 2. Organometallic chemistry (16 hours) Pd(II)-catalyzed reactions of alkenes. Reactions with water, with water and chlorides, with amines, with amides and carboxylic acids. Pd(II)-catalyzed reactions of alkynes. Reactions with amides and amines. Reactions Pd(0)-catalyzed of organic halides and pseudo halides. Reactions with alkenes (Heck reaction), with alkynes, with boronic acids or esters (Suzuki reaction), with nitrogen-containing nucleophiles (Buchwald-Hartwig eaction). Olefin metathesis, Schrock’s catalyst, Grubbs catalyst. Reaction mechanism . RCM, ROM, ADMET, ROMP, CM reactions. Rules for selectivity. Section 3. Bioorganic chemistry (4 hours) Classification of bioorganic reactions. Representative examples. Section 4. Retrosynthesis (4 hours) Disconnections. Retrosynthetic analysis of aromatic compounds. C-X disconnections. Umpolung. Protective group. C-C disconnection. (1,1 C-C, 1,2 C-C, 1,3 C-C, 1,5 C-C). Functional group interconversion (FGI). Section 5. NMR Spectroscopy (8 ore) Introduction to 1D and 2D NMR Spectroscopy; determination of enantiomeric excess via NMR spectroscopy; structural determination of intermediate complexity molecules.
Prerequisites
To fully benefit from the SACO lectures, students should possess the knowledge acquired in the Organic Chemistry I and II courses and Physical Methods in Organic Chemistry. This includes: basic and advanced stereochemistry, reactivity of organic functional groups, main reaction mechanisms, inter- and intramolecular acid and nucleophilic catalysis, and interpretation of 1D-NMR spectra (¹H and ¹³C).
Books
For section 1 and 3: “Advanced Organic Chemistry”; F. A. Carey, R. J. Sundberg, Plenum Publishing Corporation, ISBN 0-306-43457-1. For section 2: “Organometallics in Synthesis”; M. Schlosser, John Wiley & Sons. ISBN 0-471-93637-5; “Palladium Reagents and Catalysts” J. Tsuji. John Wiley & Sons, ISBN 0-470-85033-7. For section 4: “Organic Synthesis: The Disconnection Approach”; S. Warren. John Wiley & Son. ISBN 978-0470712269.
Frequency
Attendance at lectures, although highly beneficial for achieving the learning objectives of the course, is not mandatory.
Exam mode
The final exam can be: a) Traditional, consisting of an oral exam with open-ended questions, which ends with a grade out of thirty; the final grade will take into account the following elements: 1. Knowledge of the entire course material; 2. Ability and clarity in presenting the topics; 3. Ability to connect and synthesize the various topics. b) Preparation and presentation of a brief thesis, on a topic agreed upon with the instructor, related to the subjects covered in the course. The grade out of thirty will reflect: 1. Level of understanding of the topics covered in the thesis that were treated during the course; 2. Clarity in presenting the covered topics. Regardless of the chosen exam format, passing the exam with the minimum grade requires a sufficient understanding of the topics covered in the various parts of the syllabus. To achieve a grade of 30/30 with honors, the student must demonstrate an excellent understanding of all the topics covered during the course, and the ability to logically and coherently connect them. There is no maximum number of exam attempts allowed during the academic year.
Lesson mode
Teaching is delivered in a combined format, both in person and via videoconference. A typical lecture is conducted using course slides, which have been originally prepared by the instructor and are subject to annual revision. The lecture is supplemented with in-depth content presented to students using the electronic whiteboard in the classroom.
  • Lesson code10612259
  • Academic year2025/2026
  • CourseIndustrial pharmacy
  • CurriculumSingle curriculum
  • Year5th year
  • Semester1st semester
  • SSDCHIM/06
  • CFU6