2.10 Chiral Pool Synthesis: Chiral Pool Synthesis from Hydroxy Acids: Lactic Acid, Tartaric Acid, Malic Acid, and 2-Methyl-3-hydroxypropionic Acid

Abstract

The following chapter covers hydroxy acids, which are derived from the chiral pool. Their application in recent natural product synthesis will be reviewed. Several examples for each hydroxyl acid were chosen particularly with regard to substrate controlled diastereoselective reactions. For a better understanding of the presented syntheses the molecular framework of the chiral pool building blocks are marked in blue throughout the whole synthesis. In this way the reader is able to track the disposition of the initial fragments. Each section starts with a short introduction to the corresponding hydroxy acid, primarily focusing on the industrial production. The following hydroxy acids are dealt with: 3-hydroxybutyric acid, lactic acid, methyl (R)-(−)-3-hydroxy-2-methylpropionate (Roche ester), mandelic acid, malic acid, and tartaric acid.