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Retrosynthetic analysis is a technique for solving problems in the planning of organic syntheses. This is achieved by transforming a target molecule into simpler precursor structures without assumptions regarding starting materials. Each precursor material is examined using the same method. This procedure is repeated until simple or commercially available structures are reached. E.J. Corey formalized this concept in his book The Logic of Chemical Synthesis.  
The power of retrosynthetic analysis becomes evident in the design of a synthesis. The goal of retrosynthetic analysis is structural simplification. Often, a synthesis will have more than one possible synthetic routes. Retrosynthesis is well suited for discovering different synthetic routes and comparing them in a logical and straightfoward fashion.
Additional recommended knowledge
An example will allow the concept of retrosynthetic analysis to be easily understood.
In planning the synthesis of phenylacetic acid, two synthons are identified. A nucleophilic "-COOH" group, and an electrophilic "PhCH2+" group. Of course, both synthons do not exist per se; synthetic equivalents corresponding to the synthons are reacted to produce the desired product. In this case, the cyanide anion is the synthetic equivalent for the -COOH synthon, while benzyl bromide is the synthetic equivalent for the benzyl synthon.
The synthesis of phenylacetylene determined by retrosynthetic analysis is thus:
Functional Group Strategies
Manipulation of functional groups can lead to significant reductions in molecular complexity.
Numerous chemical targets have distinct stereochemical demands. Stereochemical transformations (such as the Claisen rearrangement and Mitsunobu reaction) can remove or transfer the desired chirality thus simplifying the target.
Directing a synthesis toward a desirable intermediate can greatly narrow the focus of an analysis. This allows bidirectional search techniques.
The application of transformations to retrosynthetic analysis can lead to powerful reductions in molecular complexity. Unfortunately, powerful transform-based retrons are rarely present in complex molecules, and additional synthetic steps are often needed to establish their presence.
The identification one or more key bond disconnections may lead to the identification of key substructures or difficult to identify rearrangement transformations.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Retrosynthetic_analysis". A list of authors is available in Wikipedia.|