jo302308q_si_001.pdf (2.26 MB)

Synthesis of the 1‑Monoester of 2‑Ketoalkanedioic Acids, for Example, Octyl α‑Ketoglutarate

Download (2.26 MB)
journal contribution
posted on 07.12.2012, 00:00 by Michael E. Jung, Gang Deng
Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of α-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.