Advance pharmaceutical organic chemistry: Course Outline (901)

Stereochemistry

• Elements of symmetry
• Plane of symmetry and center of symmetry
• Alternating axis of symmetry
• Simple axis of symmetry

Kinds of molecules displaying optical activity

• Compounds with a chiral carbon atom
• Compounds with other quadrivalent chiral atoms
• Compounds with tervalent chiral atoms suitably substituted adamantanes​

Optical isomerism in compounds containing no chiral atom

• Biphenyls
• Allenes
• Compounds with exocylic double bonds
• Spiranes
• Chirality due to a helical shape
• Chirality caused by restricted rotation of other types

Cis-trans isomerism

• Resulting from double bonds
• Monocyclic compounds
• Fused ring systems
• Out-in isomerism
• Enantiotopic and diastereotopic atoms
• Groups and faces chirality and importance of chiral drugs
• Techniques for preparing chiral drugs (chirality pool
• Enzymatic transformation and assymetric synthesis)

Rearrangements

• Carbon to carbon migration
• Carbon to oxygen and oxygen to carbon migration
• Nitrogen to carbon
• Oxygen to carbon migrations

Elimination reactions

• E2 E1 and E1cb mechanisms
• Orientation effects in elimination reactions stereochemistry of E2 elimination reactions elimination not involving C-H bonds

Substitution reactions

Electrophilic aromatic substitution

• Nitration
• Halogenations​

Friedel crafts alkylations and acylations 

nucleophilic aromatic substitution

• Aromatic diazonium ions as synthetic intermediates
• Substitution by the addition-elimination mechanism
• Substitution by the elimination-addition mechanism
• Substituion by the SN1 mechanism
• Additions reactions