StereoselectiveSynthesis of (<i>R</i>)‑all-<i>trans</i>-13,14-Dihydroretinol and -Retinoic Acid

Vitamin A (or all-<i>trans</i>-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 (<i>R</i>)-all-<i>trans</i>-13,14-dihydroretinol and -retinoic acid, applying an <i>E</i>-selective HWE olefination and a Ru(II) catalyzed intramolecular 7-<i>endo</i>-<i>dig</i> hydrosilylation as the key steps.

Publication Details

Journal
Figshare
Published
2025-02-20
DOI
https://doi.org/10.1021/acs.joc.4c03173.s001
Primary Topic
Retinoids in leukemia and cellular processes
Type
article
Field-Weighted Citation Impact
0.00
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article

StereoselectiveSynthesis of (R)‑all-trans-13,14-Dihydroretinol and -Retinoic Acid

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Retinoids in leukemia and cellular processes
article

StereoselectiveSynthesis of (R)‑all-trans-13,14-Dihydroretinol and -Retinoic Acid

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Abstract

Vitamin A (or all-<i>trans</i>-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 (<i>R</i>)-all-<i>trans</i>-13,14-dihydroretinol and -retinoic acid, applying an <i>E</i>-selective HWE olefination and a Ru(II) catalyzed intramolecular 7-<i>endo</i>-<i>dig</i> hydrosilylation as the key steps.

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Openalex Percentile: Top 61%
Retinoids in leukemia and cellular processes
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StereoselectiveSynthesis of (<i>R</i>)‑all-<i>trans</i>-13,14-Dihydroretinol and -Retinoic Acid · Figshare (2025) | TGRS Research Map | TGRS