Chiral pool synthesis
From Wikipedia, the free encyclopedia
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
Principles: Chirality, Stereoisomer, Enantiomer, Diastereomer
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
 |
This chemistry article is a stub. You can help Wikipedia by expanding it. |
