Asymmetric Synthesis of Homocitric Acid Lactone.

The Journal of organic chemistry

PubMedID: 27685496

Nickerson LA, Huynh V, Balmond EI, Cramer SP, Shaw JT. Asymmetric Synthesis of Homocitric Acid Lactone. J Org Chem. 2016;.
A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bio-inspired aldol addition to set the stereogenic center in an intermediate that only requires modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.