Semester-IV

Designing of organic synthesis: Protection and de-protection of hydroxyl, amino, carboxyl, ketone and aldehyde functions as illustrated in the synthesis of polypeptide and polynucleotide, enamines, Umpolung in organic synthesis, Reterosynthesis.

Principles and applications of asymmetric synthesis: (24L) stereoselectivity in cyclic compounds, enantio-selectivity, diastereo-selectivity, enatiomeric and diastereomeric excess, stereoselective aldol reactions. Cram’s rule, Felkin Anh rule, Cram’s chelate model, Asymmetric synthesis, use of chiral auxiliaries, chiral reagents and catalysts, asymmetric hydrogenation, asymmetric epoxidation and asymmetric dihydroxylation.

Basic understanding with hands-on training of the various chromatographic techniques

Paper and Thin layer chromatography (TLC)

Gas Chromatography (GC)

High Performance Liquid Chromatography (HPLC)

Gas Chromatography–Mass Spectrometry (GC-MS)

Liquid Chromatography–Mass Spectrometry (LC–MS)

CHO-451: Advanced Synthetic Organic Chemistry

Section I-

1. Structure and stereochemistry of Hardwickiic acid, Camptothecin and podophyllotoxin 

 2. Synthesis of i) Taxol ii) Estrone and Mifepristone  iii) Juvabione (K.Mori and Matsui, Pawson and Cheung Synthesis) iv) Fredericamycin A 

 Section II-

 Biogenesis – The building blocks and construction mechanism of 

 1. Terpenoids – Mono, Sesqui, Di and Triterpenoids and cholesterol

 2. Alkaloids derived from ornithine, lysine, nicotinic acid, tyrosine and tryptophan.

 3. The shikimate pathway – cinnamic acids, lignans and lignin, coumarins, flavonoids and stilbens, isoflavanoids and terpenoid quinones.