By Ashutosh Kar
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Extra info for Advanced Practical Medicinal Chemistry
The importance of the basic carbon skeleton present in the conceived and proposed target-drug-molecule structure in any synthesis, cannot be ruled out. It may be accomplished through a series of reactions that eventually form the vital links to the newly proposed carbon skeleton. J. , New York, 1989. P-IV\C:\N-ADV\CH2-1 DRUG SYNTHESIS 17 termed as the construction reactions, is regarded as the backbone and obviously the most crucial step in designing a synthesis. (b) Inclusion of Functional Moieties.
The carbanion [I] is formed much faster than the rather simple carbanion (R : –) which would be generated from a simple carboxylate ion (RCOO–) because it is relatively more stable. Its greater stability is on account of the accomodation of the negative charge by the keto function. P-IV\C:\N-ADV\CH2-2 36 ADVANCED PRACTICAL MEDICINAL CHEMISTRY Interestingly, the decarboxylation of free acetoacetic acid (II) specifically involves O transfer of the acidic hydrogen to the corresponding keto C moiety in two manners, F GG H I JJ K namely : (a) Prior to loss of CO2 , and (b) Simultaneously with loss of CO2, as illustrated below : Note : It is known that the function of protonation is to minimise the basicity of a leaving group.
Michael, J. Prakt. ,  35, 349 (1887). , Tetrahedron Asymmetry, 3, 459–505 (1992). P-IV\C:\N-ADV\CH2-2 DRUG SYNTHESIS 37 The various types of donors, acceptors and bases that are used in Michael Reaction are stated as under : DONORS. Acetoacetates ; Aldehydes ; Carboxylic esters ; Cyanoacetates ; Ketones ; Malonates ; Nitriles ; Nitro compounds ; and Sulfones. ACCEPTORS. Aldehydes ; Amides ; Carboxylic acids ; Esters ; Nitriles ; Nitro compounds ; Phosphonates ; Phosphoranes ; Sulphoxides ; Sulphones ; and α, β-Unsaturated ketones.