Synthon Approach – (2 Hr/Wk)
Course Objectives
1. To teach the learner to analyse a target structure in order to design a synthetic scheme.
2. To acquire the expertise toward synthesis by the manipulation of both activation methods and selectivity control.
Course Outcomes
1. Learner will also gain confidence for drawing the schematic retrosynthetic pathway from the course.
2. Learner will be able to analyze the retrosynthetic scheme synthesis planning and route analysis for any given target molecule.
1. Definition of retrosynthesis or disconnection approach, synthon, disconnection, synthetic equivalent, functional group interconversion, functional group addition, functional group removal.
1
2. Guidelines for disconnection
a. Order of events
b. Reversal of polarity
c. Protecting groups
Disconnection of simple alcohols, alkyl halide, ethers, olefins, esters, carboxylic acids,
aldehydes, ketones and amines.
Two group disconnections – 1,2-, 1,3-, 1,4- difunctionalized compounds
Strategies for synthesis of aromatic heterocycles pyrrole, thiophene, furan, pyridine,
pyrimidine
4 Design of retrosynthesis of drugs: Paracetamol, benzocaine, sulfadiazine, ibuprofen,
propranolol, nifedipine, isoniazid, ranitidine, diphenhydramine
Synthon Approach Course Syllabus & Textbooks:
1. Designing organic syntheses: A programmed introduction to the synthon approach, Stuart Warren; Wiley India Pvt Ltd., 2012
2. Designing Organic Syntheses: A Programmed Introduction to the Synthon Approach; Stuart Warren; ISBN: 978-0-471-99612-5,
285 pages, January 1991
3. Organic Synthesis the Disconnection Approach, Stuart Warren, 391pages, ISBN 0 471 10161 3 Paper 1982 by John Wiley and Sons
LTD
4. Synthesis of Drug, A synthon approach by Radhakrishnan P. Iyer & Anant v. prabhu, 1st Edition, (1985) Sevak Publications,
Mumbai.
5. Clayden and Greeves, Organic Chemistry, Oxford University Press (2001)
6. site for solving synthon problems
http://highered.mheducation.com/sites/0073375624/student_view0/chapter22/synthesis_problem_1-2.html