Chiral pool synthesis
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Chiral pool synthesis is a strategy that aims to improve the efficiency of chiral synthesis. It starts the organic synthesis of a complex enantiopure chemical compound from a stock of readily available enantiopure substances. Common chiral starting materials include monosaccharides and amino acids. The built-in chirality is then preserved in the remainder of the reaction sequence.
This strategy is especially helpful if the desired molecule bears a great resemblance to cheap enantiopure natural products. Otherwise, a long, tortuous synthesis involving many steps with attendant losses in yield may be required. At times, it may be difficult to find a suitable enantiopure starting material; other techniques may prove more fruitful.
General methods used in chiral pool synthesis are the use of protecting groups, and functional group interconversion (FGI).
[edit] Examples
Chiral pool synthesis is used to build a part of the epothilone molecule (an alternative to Paclitaxel), from readily available enantiopure (-)-pantolactone.[1]
[edit] See also
| Concepts in asymmetric synthesis | |
|---|---|
| Analysis: | Optical rotation, Enantiomeric excess, Diastereomeric excess, Chiral derivitizing agents |
| Chiral resolution: | Crystallization, Kinetic resolution, Chiral column chromatography |
| Reactions: | Asymmetric induction, Chiral reagents, Chiral pool synthesis, Chiral auxiliaries, Asymmetric catalytic reduction, Asymmetric catalytic oxidation, Organocatalysis, Biocatalysis |
[edit] References
- ^ Ulrich Klar, et al, Efficient Chiral Pool Synthesis of the C1-C6 Fragment of Epothilones, Synthesis, 2005: 301-305. DOI:10.1055/s-2004-834936
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