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

Kazuhiro Sugamoto; Ryoya Nishikawa; Tomonori Nakanishi

doi:10.2174/0115701786370905250228040842

ISSN: 1570-1786
E-ISSN: 1875-6255

Synthesis of (2R,6R,10R)- and (2S,6R,10R)-Pristanic Acid Diastereomers
Authors: Kazuhiro Sugamoto¹, Ryoya Nishikawa² and Tomonori Nakanishi³
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¹ Department of Applied Chemistry, Faculty of Engineering, University of Miyazaki, Gakuen-Kibanadai, Miyazaki 889-2192, Japan ; ² Graduate School of Engineering, University of Miyazaki, Gakuen-Kibanadai, Miyazaki 889-2192, Japan ; ³ Department of Biochemistry and Applied Biosciences, Faculty of Agriculture, University of Miyazaki, Miyazaki 889-2192, Japan
Source: Letters in Organic Chemistry, Volume 22, Issue 8, Aug 2025, p. 591 - 595
DOI: https://doi.org/10.2174/0115701786370905250228040842
- Received: 04 Dec 2024
- Accepted: 03 Jan 2025
- Available online: 03 Mar 2025

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.

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

Lett. Org. Chem. 22, 591 (2025); https://doi.org/10.2174/0115701786370905250228040842

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Article Type: Letter

Keyword(s): (2R,6R,10R)-pristanic acid; (2RS,6R,10R)-pristanic acid; (2S,6R,10R)-pristanic acid; dehomologation; dihydrophytol; IBX

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

Abstract

From This Site

Supplementary material is available on the publisher’s website along with the published article.

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