Organic Synthesis and Chemistry of Natural Products

Paper Code: 
CHY 424 C
Contact Hours: 
45.00
Objective: 

To learn the retrosynthesis and different classes of natural products for future endeavours in organic chemistry

9.00
Unit I: 
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

9.00
Unit II: 
One and Two Group C-C Disconnections

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.

8.00
Unit III: 
Terpenoids and Carotenoids

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.

8.00
Unit IV: 
Alkaloids

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.

12.00
Unit V: 
Steroids

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

Essential Readings: 
  1. Designing Organic Synthesis; First Edition; S. Warren; John Wiley and Sons, Great Britain, 2002.
  2. Organic Synthesis- Concepts, Methods and Starting Materials; J. Fuhrhop and G.Penzillin; Verlage VCH.
  3. Some Modern Methods of Organic Synthesis; Third Edition; W. Carruthers; Cambridge Univ. Press, UK, 1987.
  4. Advanced Organic Chemistry: Reactions, Mechanisms and Structure; Fourth Edition; Jerry March; John Wiley and Sons Asia Private Limited, New Delhi, 2007
  5. Advanced Organic Chemistry Part A & B; Fourth Edition; Francis A. Carey and Richard J. Sundberg; Kluwer Academic/Plenum Publishers, New York, 2000.
  6. Organic Chemistry, Vol 2; Fifth Edition; I.L. Finar; Longman Scientific and Technical, Singapore, 1997.
  7. Rodd’s Chemistry of Carbon Compounds; Ed. S. Coffey; Elsevier.