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Retro Synthetic Analysis

Retrosynthetic analysis is a technique for planning organic syntheses by deconstructing target molecules into simpler precursor structures. Each precursor is examined using the same method of retrosynthesis until commercially available starting materials are identified. E.J. Corey formalized this concept. The power of retrosynthesis is in designing syntheses by discovering multiple synthetic routes and comparing them logically. A database can be consulted at each step to avoid exploring known compounds.

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194 views4 pages

Retro Synthetic Analysis

Retrosynthetic analysis is a technique for planning organic syntheses by deconstructing target molecules into simpler precursor structures. Each precursor is examined using the same method of retrosynthesis until commercially available starting materials are identified. E.J. Corey formalized this concept. The power of retrosynthesis is in designing syntheses by discovering multiple synthetic routes and comparing them logically. A database can be consulted at each step to avoid exploring known compounds.

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sachin1211151
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Retrosynthetic analysis

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.[1] [2] [3]

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 route. Retrosynthesis is well suited for discovering
different synthetic routes and comparing them in a logical and straightfoward fashion.[4]
A database may be consulted at each stage of the analysis, to determine whether a
component already exists in the literature. In that case, no further exploration of that
compound would be required.

Contents
[hide]

• 1 Definitions
• 2 Example
• 3 Strategies
o 3.1 Functional Group Strategies
o 3.2 Stereochemical Strategies
o 3.3 Structure-Goal Strategies
o 3.4 Transform-based Strategies
o 3.5 Topological Strategies
• 4 See also
• 5 References

• 6 External links

[edit] Definitions
Disconnection
A retrosynthetic step involving the breaking of a bond to form two (or more)
synthons.
Retron
A minimal molecular substructure that enables certain transformations.
Retrosynthetic tree
A directed acyclic graph of several (or all) possible retrosyntheses of a single
target.
Synthon
An idealized molecular fragment. A synthon and the corresponding commercially
available synthetic equivalent are shown below:

Target
The desired final compound.
Transform
The exact reverse of a synthetic reaction; the formation of starting materials from
a single product.

[edit] Example
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 phenylacetic acid determined by retrosynthetic analysis is thus:

PhCH2Br + NaCN → PhCH2CN + NaBr


PhCH2CN + 2 H2O → PhCH2COOH + NH3
In fact, phenylacetic acid has been synthesized from benzyl cyanide,[5] itself prepared by
the analogous reaction of benzyl chloride with sodium cyanide.[6]

Strategies
Functional Group Strategies

Manipulation of functional groups can lead to significant reductions in molecular


complexity.

Stereochemical Strategies

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.

Structure-Goal Strategies

Directing a synthesis toward a desirable intermediate can greatly narrow the focus of an
analysis. This allows bidirectional search techniques.

Transform-based Strategies

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.

Topological Strategies

The identification one or more key bond disconnections may lead to the identification of
key substructures or difficult to identify rearrangement transformations.

• Disconnections that preserve ring structures are encouraged.


• Disconnections that create rings larger than 7 members are discouraged.

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