D1. Knowledge and understanding of the key concepts in retrosynthesis and of the main synthetic strategies.
D2. Applying knowledge and understanding to the resolution of synthetic problems.
D3. Making judgements on sythetic strategies.
D4. Communication skills in the preparation of a synthetic plan.
D5. Learning skills on the future developments of synthetic strategies.

Organic chemistry 1 and 2 courses

1. retrosynthetic analysis 2. synthetic strategies for cyclic compounds. 3. synthetic strategies for the C-C bond by coupling reactions 4. rearrangements. 5. synthetic strategies for the C=C bond by methatesis.

S. Warren - Organic Synthesis – the disconnection approach, 2nd edition 2008, Wiley NY
Claydem, Greeves, Warren, Wothers – Organic Chemistry, 2001, Oxford
Willis, Wills – Organic Synthesis, 2003, Oxford
Smit, Bochkov, Caple – Organic Synthesis, the Science behind the Art, 1998, RSC

1. Introduction to retrosynthetic analysis: general concepts (disconnection, functional group interconversion, synthon, synthetic equivalent). Parameters of retrosynthetic analysis: carbon backbone and structural complexity degree. Symmetry and functional group correlation. Topological correlations between functional groups. Space relationships and control elements. 2. Single disconnections: alcohols (disconnection to carbonyl compound and carbon ion. Disconnection to ester and carbon ion. Reduction of carbonyl compound. Epoxide ring opening by carbon ion equivalent. Maximal structural simplification). Olefins (dehydration and regioselectivity. direct double bond disconnection. Methatesis. Alkyne hydrogenation). Carbonyl componds (alpha, beta and gamma disconnections). Acids and acid derivatives (alpha disconnections) 3. Multiple disconnections: 1,1-difunctional compounds. 1,3-difunctional compounds (aldol and related reactions; 1,3-dicarbonyls – Claisen, Mannich reactions). 1,5-difunctional compounds (Michael and Knoevenagel reactions). 1,2-difunctional compounds (olefin oxidation, pinacol reduction; alpha-hydroxyacids, alpha-hydroxyketones – non logical disconnection and synthetic equivalents of non logical synthons; alpha-halogenocarbonyls). 1,4-difunctional compounds (1,4-diketones and gamma-hydroxyketones). 1,6-difunctional compounds. 4. Coupling reactions with Pd(0) catalysts. 5. Cycles: synthetic methdologies towards cyclic compounds (Olefin methatesis, Nazarov cyclizations), small rings and polycyclic compounds. 6.Rearrangements .

Lessons in the classroom and tutorials.

Federico Berti is available at DSCF, C11 building, room 339, tel. 040 558 3920, email fberti@units.it

Two written evaluations during the course. Final written evaluation in case of unsatisfactory results. Oral test if required by the student or if the teacher requires more details on the solution of the problems. The final evaluation is formulated according to the following grid: Excellent (30 - 30 with honors): excellent knowledge of the subject, excellent command of language, the student shows excellent ability to apply the basic knowledge for solving synthetic problems. Very good (27 - 29): good knowledge of the topics, notable command of language; the student is able to correctly apply the basic knowledge. Good (24-26): good knowledge of the topics, fair command of language; the student shows an adequate ability to apply the basic knowledge. Satisfactory (21-23): the student does not show full mastery of the subject, although he/she has basic understanding of the topics; however, he/she shows sufficient command of language and sufficient ability to apply the principles. Sufficient (18-20): minimal knowledge of the subject and minimal use of technical language, limited ability to adequately apply the theoretical knowledge. Insufficient: the student does not possess an acceptable knowledge of the subject.