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Advanced Practical Medicinal Chemistry by Ashutosh Kar

By Ashutosh Kar

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From a close-look of the target-drug-molecule the researcher may logically ponder over the ways and means to accomplish their objective through the kinds of reaction(s) to make use in a sequential manner. In other words, the strategic attack on the target-drug-molecule may be conveniently and formally divided into two major components, namely : (a) Basic Carbon Skeleton. The importance of the basic carbon skeleton present in the conceived and proposed target-drug-molecule structure in any synthesis, cannot be ruled out.

4. Comprehensive Organic Chemistry, Vol. ), Pergamon, Oxford (UK), 1979. 5. M. B. S. Wingrove, ‘An Introduction to Modern Experimental Organic Chemistry’, Holt, Rienhart and Winston, New York, 1985. 6. G. Breiger, ‘A Laboratory Manual for Modern Organic Chemistry’, Harper and Row, New York, 1969. 7. T. Finley and J. , 1970. 8. D. A. ), ‘The Organic Chemistry of Drug Synthesis’, John Wiley and Sons, New York, 1995. 9. , Whitehouse Station, NJ, 12th, edn, 1996. 10. Jerry March, ‘Advanced Organic Chemistry’, John Wiley & Sons, Brisbane, 4th, edn, 1992.

Thus, from the above reaction it is quite evident that the nucleophilic substitutions (SN2 reactions) proceed with the inversion of configuration. Example. Having gathered a clear concept about ‘reaction selectivity’ one may accomplish the following two objectives by the help of nucleophilic substitutions (SN2) : (a) A chiral centre may be easily converted to one of the opposite configurations, and (b) A cis-diastereomer may be changed into a trans-diastereomer. P-IV\C:\N-ADV\CH2-2 40 ADVANCED PRACTICAL MEDICINAL CHEMISTRY The above cited example vividly shows the inversion of configuration of cis-5-hydroxy-2propyl cyclopentane into trans—isomer via step-1 through step-3.

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