Organic Synthesis and Chemistry of Natural Products

Paper Code: 
CHY 424-C
Credits: 
3
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.

7.00
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.

Definition, nomenclature, physiological action, occurrence, general methods of structure elucidation, degradation, classification based on nitrogen heterocyclic ring.

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.

 

 

References: 

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.

Academic Year: