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Faculty of Science Handbook, Session 2017/2018

application of isotopic labelling (esp. in conjunction with synthesis; selected examples from classical and
13C NMR) in the study of biosynthetic processes. contemporary syntheses.
Biosynthesis of selected natural products: polyketides, Assessment Methods:
fatty acids, prostanoids, aromatic compounds (e.g. Continuous assessment: 30%
Shikimic acid), macrocyclic antibiotics, terpenes, Final examination: 70%
terpenoids, and natural rubber; biosynthetic pathways,
reaction types, and mechanistic aspects (esp. enolate- Medium of instruction:
carbonyl reactions and biochemical cascades). English
Assessment Methods: Soft skills:
Continuous assessment: 30% CT1-3
Final examination: 70%
References:
Medium of instruction: 1.Stuart Warren, Organic Synthesis: The Disconnection
English Approach, John Wiley and Sons, Chichester, New York,
Brisbane, Toronto, Singapore, 1982.
Soft skills: 2.F. A. Carey and R. J. Sundberg, Advanced Organic
CT1-3 Chemistry, Part B: Reactions and Synthesis, 4 th ed.,
Plenum Press, New York & London, 2002.
References: 3.M. B. Smith, Organic Synthesis, 2 nd ed., McGraw Hill
1.H. S. Stoker, General, Organic and Biological Inc, 2001.
Chemistry, 5 ed., Brooks/Cole, 2010. 4.M. B. Smith and J. March, March's Advanced Organic
th
2.D. Voet, and J. G. Voet, Biochemistry. 3 rd ed., Wiley, Chemistry: Reactions, Mechanisms, and Structure
2004. (March's Advanced Organic Chemistry), 5 ed., Wiley-
th
3.Bu’Lock and B. G. Kurt Kimia Hasil Semulajadi, DBP, Interscience; 2001.
Kuala Lumpur. 5.W. A. Smit, A. F. Bochkov and R. Caple, Organic
4.J. Mann, Secondary Metabolism, 2 nd ed., Oxford Synthesis: The Science Behind the Art, RSC, 1998.
University Press, 1987.
5.J. Mann, Chemical Aspects of Biosynthesis, Oxford
University Press, 1994. SIC3011 MECHANISTIC ORGANIC CHEMISTRY
Reactive intermediates in organic chemistry including
SIC3009 NATURALPRODUCTS CHEMISTRY carbocations, free radicals, carbenes, nitrenes, and
radical-ions. Chemistry of free radicals: reactions and
The influence of biosynthetic hypotheses and insights on mechanisms of free radicals including abstraction,
the syntheses of steroids. Investigation of selected natural addition, rearrangement, cyclization and fragmentation;
products such as alkaloids, terpenoids, flavonoids, applications of radical reactions in organic synthesis;
lignans, glycosides. Semiochemistry. Separation methods reactions of carbenes, carbenoids, nitrenes, and ion-
for natural product isolation. Spectroscopic methods for radicals, and applications in synthesis. Formation, stability,
structural elucidation of natural products. and rearrangements of carbocations; tandem and cascade
cyclizations. Mechanistic details of selected classes of
Assessment Methods: organic reactions such as nucleophilic substitution,
Continuous assessment: 30% hydrolysis, polar rearrangements, electron-transfer
Final examination: 70% reactions, photochemical reactions. Pericyclic reactions:
molecular orbitals; conservation of orbital symmetry in
Medium of instruction: concerted reactions; theory (frontier orbital method, use of
English correlation diagrams, aromatic transition state approach)
and applications of electrocyclic reactions, sigmatropic
Soft skills: rearrangements, and cycloadditions, including tandem and
CT1-3 cascade processes, in organic synthesis.
References: Assessment Methods:
1.J. Mann, Secondary Metabolism, Clarendon Press: Continuous assessment: 30%
Oxford, 1995. Final examination: 70%
2.P. M. Dewick, Medicinal Natural Products - A
Biosynthetic Approach, John Wiley & Sons, 2009. Medium of instruction:
3.E.Fattorusso, O. Taglialatela-Scafati, Eds Modern English
Alkaloids - Structure, Isolation, Synthesis and Biology;
Wiley-VCH, 2008. Soft skills:
4.J. H. Simpson, Organic Structure Determination Using CT1-3
2-D NMR Spectroscopy - A Problem-Based Approach,
Academic Press, 2008. References:
5.S. Stefan Berger, D. Sicker, Classics in Spectroscopy, 1. R. B. Woodward and R. Hoffmann, The Conservation of
Wiley-VCH, 2009. Orbital Symmetry, Academic Press Inc, 1970.
2. J. Clayden, N. Greeves, S. Warren, P. Wothers,
Organic Chemistry, Oxford.
SIC3010 ORGANIC SYNTHESIS 3. J. March, and M. Smith, Advanced Organic Chemistry,
th
6 ed., New York: John Wiley & Sons, 2007.
Retrosynthetic analysis and synthesis design. Selectivity 4. T. H. Lowry and K. S. Richardson, Mechanism and
rd
in synthesis: chemo-, regio-, and stereoselectivity. Theory in Organic Chemistry, 3 ed., Harper and Row,
Synthesis of acyclic and cyclic compounds. Concept of 1987.
umpolung; functional group interconversion. Use of 5. A. J. Bellamy, An Introduction to the Conservation of
organometallic reagents in syntheses. Asymmetric Orbital Symmetry, Longman, 1974.

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