Organic Synthesis and Chemistry of Natural Products

Disconnection Approach and Protecting Group

An introduction to synthons and synthetic equivalents, disconnection approach, functional group inter-conversions, the importance of the order of events in organic synthesis, one group C-X and two group C-X disconnections, chemoselectivity, reversal of polarity, cyclisation reactions, amine synthesis; principle of protection of alcohol, amine, carbonyl and carboxyl groups.

Self study: Name reactions

Alcohols and carbonyl compounds, regioselectivity, alkene synthesis, uses of alkynes and aliphatic nitro compounds in organic synthesis; Diels’ Alder reaction, 1,3-difunctionalised compounds, α,β-unsaturated carbonyl compounds, control in carbonyl condensations, 1,5-difunctionalised compounds; Micheal addition and Robinson annelation.

Classification, nomenclature, occurrence, general methods of structure determination, isoprene rule; structure determination, stereochemistry and synthesis of the following representative molecules – Citral, Geraniol, Menthol and β-Carotene.

Definition, nomenclature, physiological action, occurrence, general methods of structure elucidation, degradation, classification based on nitrogen heterocyclic ring. Structure, stereochemistry and synthesis of the following – Ephedrine, (+)-Nicotine and Morphine.

Self Study: Role of alkaloids in plants.

Occurrence, nomenclature, basic skeleton, Diels’ hydrocarbon and stereochemistry. Structure determination and synthesis of Cholesterol, Androsterone, Testosterone, Estrone.