45074 - Chemistry, Biosynthesis and Characterisation of Natural Substances

Learning outcomes

This course wants to furnish some information on the chemical synthesis, biosynthesis and characterization of the most important classes of natural substances.
Some details on the structural determination and the total synthesis of some famous natural product, such as quinine, daunomycin and taxol will also be furnished.

Course contents

The following compounds will be described:
1) pheromones: structure and synthesis;
2) prostaglandins: classification, synthesis and biosynthesis;
3) terpenes: classification and biogenesis;
4) sterols and corticoid and sexual hormones: structure, biogenesis and chemical synthesis;
5) aromatic polyketides: biogenesis of phenols (low molecular weight) and anthraquinones (high molecular weight);
6) shikimic acid derivatives and flavonoids;
7) alkaloids: classification and biogenesis;
8) antibiotics: penicillins, tetracyclines, streptomycins and macrolides.

Le structural determinations and some famous syntheses of daunomycin, taxol and quinine will also be described.

Readings/Bibliography

Paul M. Dewick - Chimica, Biosintesi e Bioattività delle Sostanze Naturali - Piccin
John McMurry, Tadhg Begley - Chimica Bio-organica - Zanichelli
K. C. Nicolaou, E. J. Sorensen - Classics in Total Synthesis - VCH

Teaching methods

Frontal lessons.
All the topics listed in the program will be covered with particular regard to a comparison between synthetic and biosynthetic pathways that lead to natural compounds.
The students are encourage to produce short papers on selected topics.

Assessment methods

The preparation is tested by an oral exam, whose aim is to verify the knowledge of the theoretical lessons.

Teaching tools

Overhead projector, PC, video projector

Office hours

See the website of Claudia Tomasini