Work

Synthesis of (2R,6R,10R)- and (2S,6R,10R)-Pristanic Acid Diastereomers

Year: 2025

Type: article

Abstract: In this study, the synthesis of (2S,6R,10R) and (2R,6R,10R) diastereomers of pristanic acid is described. The key step in this synthesis is the dehomologation of (3RS,7R,11R)-dihydrophytol to one-carbon shorter (2RS,6R,10R)-pristanic acid using o-iodoxybenzoic acid. The diastereomeric mixture of pristanic acid is easily separated by silica gel column chromatography after conversion to the corresponding amides, which can be converted back to (2R,6R,10R)- and (2S,6R,10R)-pristanic acids in good yields.

Source: Letters in Organic Chemistry

DOI: 10.2174/0115701786370905250228040842

Authors: Kazuhiro Sugamoto, Ryoya Nishikawa, Tomonori Nakanishi

Institution: University of Miyazaki

Language: English

Topic: Steroid Chemistry and Biochemistry

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: Japan Society for the Promotion of Science

Award: Functional evaluation of phytanic acid diastereomers