Asymmetric Synthesis of Homocitric Acid Lactone

Abstract

A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only 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.

Engineered Biosynthesis of Alkyne-Tagged Polyketides by Type I PKSs

“…All reagents were purchased from commercial suppliers and used without further purification. (R)-3-Acetyl-4benzyl-2-oxazolidinone (S3) was synthesized according to Nickerson et al (Nickerson et al, 2016) and the spectra matched reported literature values (Ager et al, 1996). Reaction progress was monitored by thin-layer chromatography on silica gel 60 plates (aluminum back, EMD Millipore) and visualized by UV light or stained with KMnO4.…”

Engineered Biosynthesis of Alkyne-Tagged Polyketides by Type I PKSs

“…General synthetic methods: All reagents were purchased from commercial suppliers and used without further purification. (R)-3-Acetyl-4benzyl-2-oxazolidinone (S3) was synthesized according to Nickerson et al (Nickerson et al, 2016) and the spectra matched reported literature values (Ager et al, 1996). Reaction progress was monitored by thin-layer chromatography on silica gel 60 plates (aluminum back, EMD Millipore) and visualized by UV light or stained with KMnO4.…”

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

“…This compound 42.3 was converted to homocitric acid lactone 42.4 in 71% yield by hydrolysis of the aldol adduct to the methyl ester using sodium methoxide, followed by oxidative cleavage and hydrolysis with acid (Scheme 42). [52] …”