# Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid

**Authors:** Paul Wienecke, Adriaan J. Minnaard

PMC · DOI: 10.1021/acs.joc.4c03173 · The Journal of Organic Chemistry · 2025-02-20

## TL;DR

Scientists developed a new way to make specific vitamin A metabolites, which could help study their roles in the body.

## Contribution

The paper introduces a stereoselective synthesis method for two vitamin A metabolites using specific chemical reactions.

## Key findings

- A stereoselective synthesis of (R)-all-trans-13,14-dihydroretinol was successfully achieved.
- The synthesis of (R)-all-trans-13,14-dihydroretinoic acid was also accomplished using key catalytic reactions.
- The method uses E-selective HWE olefination and Ru(II)-catalyzed hydrosilylation as critical steps.

## Abstract

Vitamin A (or all-trans-retinol) metabolites
are
involved in a wide range of cellular processes. However, the investigation
of their biological role is hampered due to their very limited availability.
Herein we report a stereoselective total synthesis of the vitamin
A metabolites (R)-all-trans-13,14-dihydroretinol
and -retinoic acid, applying an E-selective HWE olefination
and a Ru(II) catalyzed intramolecular 7-endo-dig hydrosilylation as the key steps.

## Linked entities

- **Chemicals:** all-trans-retinol (PubChem CID 445354)

## Full-text entities

- **Chemicals:** (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid (-), Vitamin A (MESH:D014801)

## Full text

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## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11894646/full.md

## References

30 references — full list in the complete paper: https://tomesphere.com/paper/PMC11894646/full.md

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Source: https://tomesphere.com/paper/PMC11894646